Tax Guide Rental Properties 2019

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Rental Property
Tax Guide

2019 EDITION
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1

1 The Basics P 4

Overview

2 Establishing a Home Office P 6
3 Entity Selection P 8
4 Travel Expenses P 10
5 Real Estate Tax Strategies P 16
6 Capital Improvements vs. Repairs & Maintenance Expenses P 19
7 Depreciation P 21
8 Passive Losses, Passive Activity Limits & The Real Estate

Professional Status P 24
9 Capital Gains Tax and Depreciation Recapture P 28
10 Key Tax Issues for Short-Term Rentals P 35
11 20% Pass-Through Deduction P 38
12 Casualty Losses P 40

Introduction

T

he first part of effective tax strategy and planning is understanding that when

This guide gives rental
property owners tax
strategies to minimize
next year’s bill and tips
for preparing and
understanding 2018
tax filings.

you file your tax returns each year, you’re simply reporting the results (income,

losses, etc.) of your activities from the prior year. Once the year ends, while there are
a few things that can be done, most of your results are already set in stone and you
will pay tax based on those results.
That means you need to be taking a proactive approach to tax strategy and planning
by implementing strategies and taking the right actions throughout the year so you’ll
end up with favorable results come tax filing season.
This guide is designed to give rental property owners tax strategies you can implement
now to minimize next year’s tax bill. You’ll also come away with a more precise and
nuanced understanding of your 2018 tax filing.

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3

The Basics

TAX CUTS
& JOBS ACT CHANGE
H E L O C I N T E R E ST
The Tax Cuts & Jobs Act no longer
allows you to deduct interest from

Before we get too granular, let’s cover some of the basic real estate tax

a home equity line of credit (HELOC)

strategies that have served rental property owners well for decades.

unless it was used to acquire a
residence or substantially improve

RE CORDKEEP I NG

a residence.

While it isn’t necessarily a tax strategy, the importance of keeping organized,

However, if you use a HELOC to

detailed, and up to date records cannot be understated. Doing so will allow you

fund your rental business, the interest

to see how much income your rentals are bringing in at any given time, and also

will be tax deductible if you elect

allows you to project future income and expenses. This is key in determining the

to “treat the debt secured by your

amount of estimated tax payments you’ll need to make, your tax bracket and

residence as not secured by your

the tax strategies that make the most sense for you. Luckily you have this guide

residence.” It sounds confusing but

and Stessa to help keep your accounting records up to date.

of course makes perfect sense to
the IRS, because the interest tracing
rules allow you to deduct interest if
used for business purposes.

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4

COMMON TAX D ED UCTI BLE EX PEN S ES
Below is a table of the most common tax deductible expenses you’ll want to track throughout the year.

Advertising/Marketing

Repairs and Maintenance

Leasing Commissions

Insurance

Professional Fees (Legal, Accounting, etc.)

Property Management Fees

Interest (Mortgage & Other)

Supplies

Taxes (Property & Other)

Utilities (Oil, Gas, Electric, Water, Phone, etc.)

Depreciation

Home Office Expenses

Business Mileage

Travel Expenses

Education & Training

Snow Removal, Landscaping, Pest Control, etc.

Bank Fees

HOA Fees

Employees and Independent Contractors

Business Meals (50% deductible)

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Establishing a Home Office
As a rental property owner you can

often the case for real estate investors,

dedicate a room, or a portion of a

you can still deduct the home office if

room, to a home office to secure a

it is the location you handle your

home office deduction.

administrative work (i.e. bookkeeping).

Having a home office also allows you to

IRS Rev. Proc. 2013-13 allows for a “safe

deduct local transportation expenses.

harbor” deduction for anyone with an

Without a home office, a trip from

established home office. The deduction

your home to the business site will

is $5 per sqft of the home office annually.

(2) regularly and exclusively as

Alternatively, you can use the actual

a place to meet or deal with

expense method which allows you to

patients, clients, or customers

deduct a portion of your actual home

in the normal course or trade

RE QUIRE MENTS

expenses. Divide the square footage of

of business.

AN D B E ST P R ACTI CES

your home office by the total square

be considered a personal expense.
With the home office, the same trip
will be considered a business expense.

Note that if you work off site, which is

Per IRC § 280A, a home office
must be used:
(1) regularly and exclusively as
the principal place of business;
and

footage of your home to get the ratio.

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Then multiply the ratio by the total
amount of expenses that relate to your
entire home, to arrive at the deductible
amount for your home office.
Note that any expenses related solely

EX A M PL E: HO M E O F F ICE D E D U C T I O N
If your home office is 100 square feet and your entire home is 1,000 square feet then
you can deduct 10% (100/1,000) of the expenses that relate to your entire home.

to your home office (e.g. an office chair)

HOME OFFICE

will be 100% deductible if you use the

100 sq ft / 1000 sq ft

HOME

DEDUCTION

= 10% deduction on all home expenses

actual expense method.
In order to substantiate a home office,
you’ll want to put together a small
folder including the following:
•

A statement as to what you use your
home office for

•

A floor plan showing where the
home office is located in
your home

•

Pictures of your home office

If you plan to use the actual expense method you’ll want to track all the
expenses that relate to your entire home including but not limited to:
Utilities (Oil, Gas, Electric, Water, Phone, etc.)

Mortgage Interest (Not Principal)

Homeowner’s Insurance

Internet

Landscaping

Office Supplies

Office Furniture

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Entity Selection
As a rental property owner, you’ll most likely use a business entity to hold your
investments. This is done largely for asset protection purposes rather than tax
purposes as most are considered “pass-through” entities that don’t pay tax at the

You should almost never put

entity level. Instead, the income/losses flow through to your personal tax return

rental real estate in an S or C

(Form 1040) and are taxed based on your personal circumstances.

Corporation.

Before we jump into the most common entities that real estate investors use,
it is important to note that you should almost never put rental real estate in an
S or C Corporation.
These are corporate entities that are taxed at the entity level and often incur
negative tax consequences when assets are transferred out of the entity for estate
planning or other reasons.

S I N G L E MEMB ER LLC (S MLLC)
An SMLLC is the most common type of entity for individual real estate investors.

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SMLLCs are separate from the owner for legal purposes, but disregarded for tax purposes.
This means that the rental activity in the SMLLC is reported directly on your Schedule

The K-1 amounts are

E as if you owned the property directly under your name.

then reported on your

When using an SMLLC it is important to treat it like a real business and have business

personal tax returns

bank accounts, credit cards, etc. that are separate from your personal accounts.

(Form 1040) and you’ll

M U L T I M EMB ER LLC (MMLLC)

pay tax based on your

Investors often use an MMLLC when multiple individuals invest in rental real estate

personal circumstances.

together. MMLLCs are generally taxed as partnerships and you’ll receive your portion
of the reported income or losses on a Schedule K-1.
The K-1 amounts are then reported on your personal tax returns (Form 1040) and
you’ll pay tax based on your personal circumstances.
When using an MMLLC it is important to treat it like a real business and have business
bank accounts, credit cards, etc. that are separate from your personal accounts.
Also, prior to starting the MMLLC, you’ll want to discuss profit/loss splits, capital
contributions, and how to handle unreimbursed partnership expenses with your
partners. Be sure to document this carefully in the operating agreement.

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Travel Expenses
In general, business travel must be considered both “ordinary and necessary” to be
tax-deductible. Ordinary means it is common and accepted within the trade or
business. Necessary means it is helpful and appropriate for the trade or business.
As a real estate investor, you’ll likely travel to and from your rental properties, other
business locations, new markets, and education related events. While most of these

If you established a
home office, rental
property-related driving

activities are ordinary and necessary, it is important to understand the various

is considered business

rules for deducting travel expenses.

mileage and is tax
deductible within

LOCAL TRAVEL
Most rental property owners routinely travel to and from rental properties located
within driving distance. You might also travel to the bank, the hardware store, or to

your “tax
home.”

meet with your broker, your attorney, and so on.
If you established a home office, these miles are considered business miles and are
tax deductible within your “tax home.”

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Your “tax home” is considered the geographic location (i.e. city or locality) where you
An IRS-compliant mileage log includes:

have an established rental business.
There are generally two ways you can deduct these trips:

•

Odometer reading as of Jan 1

•

Odometer reading as of Dec 31

For each business trip:

1) Using the actual expense method, or
2) The standard mileage deduction.
Both methods require you to keep an IRS-compliant mileage log.
Remembering to log the trip each time you drive somewhere for business can be a

•

The date

challenge. Use an automatic mileage tracking app like MileIQ in tandem with Stessa’s

•

The purpose

mileage expense feature to make sure you’re not missing any deductible miles.

•

The amount of miles

•

Locations

S T A N D A R D M IL EA G E R A T E
The standard mileage rate is the simplest way to deduct local travel expenses
because it requires the least amount of tracking. Simply take the amount of miles you
drove for business and multiply it by the standard mileage rate to get your deduction.
The standard deduction for 2018 is 54.5 cents per mile for 2018 and 58 cents
per mile for 2019.
The only actual expenses you can deduct under this method, in addition to the
mileage, are parking fees, tolls, interest on a car loan, and personal property tax
on the vehicle.

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In order to use the standard mileage rate, you must use it in the first year you use

E XAMPLE: ACTUAL
E XPENS E METHO D
You drive a total of 10,000 miles in
2018. 6,700 are business miles.
Your business percentage for the
vehicle is 67% (6,700/10,000).
After tallying up all the expenses

your vehicle for business purposes, otherwise you can only use the actual expense
method. However, you can later switch to the actual expense method, and back
again, so it’s generally best to start with the standard mileage rate.

A CT UA L EXPEN SE MET HOD
Under the actual expense method, you can deduct a portion of your actual expenses
from operating your vehicle. These expenses include, but are not limited to:

related to your vehicle, the total is
$8,000 for the year. You can deduct
$5,360 for 2018 ($8,000 x 67%).
BUSINESS MILES

TOTAL MILES

( 6700 / 10,000 )
X
VEHICLE EXPENSE

Car Washing

Interest on Car Loans

Tolls and Parking Fees

Gas and Oil

Other Fees (e.g. Registration Fees)

Repairs and Maintenance

Depreciation

Insurance

$8,000
=
ACTUAL EXPENSE DEDUCTION

$5,360

Lease Payments

NOT E
Tickets and violations are NOT tax deductible.

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Your deduction is based on the percentage of actual miles driven that you used your
vehicle for business. This percentage is determined by dividing the amount of miles
you drove for business by the total miles you drove for the year (business miles/total
business and personal miles). You will also need to keep records (e.g. receipts) of all
other auto expenses throughout the year.
Stessa’s mobile app can help with this as it includes OCR and machine learning to
capture and automatically categorize receipts for free.

T R A V E L T O NEW MAR K ETS
Travel expenses are treated a bit differently when traveling to a new market outside
of your tax home.
Travel expenses incurred to research and evaluate any new property that you eventually
purchase outside of your tax home, will be added to the basis of the property
and depreciated over 27.5 years. Once you purchase a rental property in the new
geographic area, additional new travel to the same area to evaluate other potential
acquisitions becomes tax deductible as a business expense.
Perhaps surprisingly, travel expenses incurred to evaluate property in a new market
in which you don’t eventually purchase a property are not immediately deductible.

Stessa’s mobile app can help keep

These are considered start-up expenses that can only be deducted after purchasing

records of receipts and expenses

your first property in the new geographic area.

throughout the year.

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What Types of Travel Expenses are Deductible?
T R A N S P O R TATIO N

L ODGI NG

Transportation to and from the business destination is tax

Lodging expenses (i.e. hotel, Airbnb, etc.) on overnight

deductible.

stays that are required for sleep or rest are deductible.

This includes but is not limited to airfare, train and bus tickets,

•

Other Expenses

car expenses (see page 11).

•

Meals outside of your tax home are 50% tax deductible

Other transportation costs that are deductible include:

•

Dry cleaning

•

Phone

•

Tips

•

Other ordinary and necessary business travel expenses

•

Expenses for travel to and from the airport
(i.e. taxi, bus, etc.)

•

From the lodging area (i.e. hotel, Airbnb, etc.)
to the business location (i.e. potential rental
property, conference center, etc.)

•

Rental cars

TAX CUTS
& JOBS ACT CHANGE
Entertainment is no longer tax deductible under
The Tax Cuts and Jobs Act.

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M I XI N G PER S O NAL & B US INESS T RA VEL
When you mix business travel with personal travel, some of the expenses (i.e. airfare)
may still be tax deductible if the trip was primarily for business purposes.

EXA MP L E: B U S I N ES S
& P ER S ON A L T R A V EL

In general this means you should be spending more than half of the total number

You go on a seven day business trip

of days you’re traveling on business activities versus personal activities. A day is

to visit your out-of-state investment

considered a business day if you spend four or more hours on business activities.

portfolio and spend five days on

It’s important to note, however, that lodging expenses, meals, and other expenses
incurred during days primarily dedicated to non-business purposes, are not tax

business and the other two at
the beach.

deductible. In addition, any travel expenses for a spouse (or child) that isn’t traveling

Because the trip was primarly for

for a “bona fide” business purpose is not tax deductible.

business purposes, the entire round-trip

Also keep in mind that if the trip is primarily for personal
purposes, travel to and from the destination (i.e.
airfare) are not tax deductible but business expenses
incurred during the same trip are deductible.

airfare, plus lodging, meals and
related expenses for the five business
days are tax deductible. However, the
lodging, meals, and other expenses
from the two personal days are
not deductible.

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Real Estate Tax Strategies
Now that we covered the basics, let’s dive into some nitty gritty real estate tax strategies

This section looks at real
estate tax strategies that
will ensure you’re paying
as little tax on your rental
income as possible.

that will ensure you’re paying as little tax on your rental income as possible.
THE IMPORTANCE OF DATE PLACED IN SERVICE
When you first purchase a rental property it will be considered “placed in service”
on day one if there’s an existing tenant in the property. If there’s no existing tenant,
then the property is assumed to be not yet in service.
To place a property into service, you must meet two requirements: (1) the
property must be ready for use; and (2) the property must be available for use.
Generally, your rental is ready for use when the city or locality of your rental property
will conservatively issue a Certificate of Occupancy. The rental property is considered
available for use once it’s advertised for rent.
Rental property investors will often purchase a property vacant and in need of significant
renovations before it’s ready to rent. Any renovation costs incurred before you place

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16

the property in service must be capitalized

As mentioned above, the definition of

Note that some renovation costs will

and depreciated, generally over 27.5

ready for lease will be determined by

always be considered capital improve-

years, regardless of whether or not

the building codes in your locality, but

ments regardless of whether or not a

they are actual capital improvements or

is typically when sheetrock is on the

property has already been placed in

simply repair and maintenance expenses.

walls and the flooring is finished. In

service (e.g. replacing the entire roof).

The key point here is that costs that are
capitalized and then depreciated are
recovered over several years and then

other words, if the property is habitable
and no longer dangerous, it’s probably
also ready for lease.

P R O T I P As a best practice,
you’ll want to get in the habit of

are subject to depreciation recapture

Once the property is in service you

itemizing your invoices so that

(a 25% tax when you sell the property).

can finish the renovation and deduct

you, or your accountant, can

Regular repair and maintenance

some of the costs as repair and main-

more easily categorize these

expenses are fully deductible in the

tenance expenses in the current year.

items as repair and maintenance

year incurred and are not subject to

Other start up costs such as appliances,

expenses or capital improvements.

depreciation recapture.

which are normally considered capital

Itemized invoices are also helpful

improvements, become deductible in

in determining whether expenses

the current year under the de minimis

might qualify under

safe harbor provision of the tax code.

one of the safe harbors

The way to successfully manage this
distinction from a tax perspective is to
complete the minimum amount of work
necessary to get the property ready for
lease, then immediately advertise it
for rent.

mentioned in the next

RECE

IPT

section or for 100% bonus
depreciation.

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EXAMPLES OF RENOVATION ITEMS & WHEN TO COMPLETE:
Before you place the property in service:
•

•

Fixing structural issues (e.g. cracks in

•

Painting

the foundation)

•

Installing appliances

Replacing an entire roof, floor, bathroom,

•

Replacing a doorknob or window

•

Repairing an existing plumbing system

•

Other minor repairs

kitchen, or plumbing system
•

After you place the property in service:

Adding a deck or new HVAC system

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Capital Improvements vs. Repairs
& Maintenance Expenses
Once your property is in service, you’ll need to determine whether each repair and

For most rental property
owners, classifying repair
and maintenance expenses
as regular repairs will
maximize current year
deductions and minimze
depreciation recapture.

maintenance expense you incur should be classified as a regular expense or a
capital improvement that must be capitalized and depreciated.
Most rental property owners will prefer to have as many of these costs as possible
classified as regular repair and maintenance expenses in order to maximize current
year deductions and minimize depreciation recapture.
Next, we’ll examine the differences between these two classifications and explore
some common examples of each. But before we do, we want to make you aware of
three safe harbors that may prove useful in moving some expenses that would otherwise
be classified as capital, into the regular expenses bucket:
•

Safe Harbor for Small Taxpayers

•

Routine Maintenance Safe Harbor

•

De Minimis Safe Harbor

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C A P I T A L I MP R OV EMEN T S

We won’t go into all the details of these
three safe harbors here, but the IRS

EXAMPLES: COMMON
REPAIR & MAINTENANCE
EXPENSES

official guidance on these safe harbors
is required reading for rental property
owners that want to maximize their
current year deductions. You’ll also

Include but are not limited to:

learn quite a bit about how the IRS

Painting

approaches capital improvements versus

Fixing:

repairs & maintenance expenses.

R E P A I R S AND MAINTENANCE

A capital improvement is an addition or
change that increases a property’s value,
increases its useful life, or adapts it (or
a component of the property) to new
uses. These items fall under categories
sometimes called betterments, restorations,

•

an existing AC unit

•

a faucet or toilet

and adaptations.

Replacing:

Repairs and maintenance are

•

a few shingles on a roof

generally one time expenses that are

•

a cabinet door

incurred to keep your property habitable

•

a few planks or tiles on a floor

and in proper working condition.

•

a broken pipe

Costs incurred to:
•

inspect, or clean part of the
building structure and/or building system

•

replace broken or worn out parts
with comparable parts

EXAMPLES: CAPITAL
IMPROEMENTS
•

Additions (e.g. additional room, deck,
pool, etc.)

•

Renovating an entire room (e.g. kitchen)

•

Installing central air conditioning, new
plumbing system, etc.

•

Replacing 30% or more of a building
component (i.e. roof, windows, floors,
electrical system, HVAC, etc.)

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Depreciation
Depreciation is one of the biggest and most important deductions for rental real

Depreciation is one of
the most important
deductions because it
reduces taxable income
but not cash flow.

estate investors because it reduces taxable income but not cash flow.
For many landlords, the most important part here will be determining a property’s
depreciable basis. The goal is to allocate as much of the property’s purchase price to
the building value as possible to maximize your depreciation expense since land is
never depreciated. The portion allocated to the building will be depreciated over
27.5 years, per the IRS guidelines for residential income property.
While allocating 20% to land and 80% to the building is a common practice, under an
audit you may have to substantiate why you chose these numbers. This is commonly
done by finding the land versus building value on an appraisal or property tax card
filed with the county. You can also use comparable land sales to make this determination
or commission a cost segregation study or appraisal by a third-party professional.
Should you decide to deviate from the county tax assessor’s land versus building
value ratio, you’ll need to be prepared to support your determination in an audit
with independent documentation prepared by a third-party professional.

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CO S T S E G R EG ATIO N S TUD IES
& 100% B ONUS D EPR ECIATION

TAX CUTS
& JOBS ACT CHANGE

In a cost segregation study, certain costs previously classified as 27.5 year property,
are instead classified as personal property or land improvements, with a shorter 5,
7, or 15-year rate of depreciation that uses accelerated methods to increase your
near-term deductions. It sounds complicated but most tax accountants and some
software will do the math for you.
Generally between 20-30% of the property’s purchase price can be reclassified under

5, 7, and 15-year property is now
eligible for 100% bonus depreciation,
which means its entire cost can
be written off in the first year
of ownership.

these shorter class lives which can significantly increase a property’s depreciation
expense. Thanks to The Tax Cuts and Jobs Act, 5, 7, and 15-year property is now eligible
for 100% bonus depreciation, which means its entire cost can be written off in the
first year of ownership.

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It’s important to note that cost segregation
studies make the most sense for

EXAMPLE: COST SEGREGATION

landlords who are considered real

A building with a value of $100,000 will typically have $3,636 in annual depreciation

estate professionals for tax purposes

($100,000/27.5). However, if you were to commission a cost segregation study and

or expect to come in under the passive

find that 20% of the building’s value can be reclassified as personal property or

loss limits discussed below.

land improvements, you could then deduct $20,000 in 100% bonus depreciation,
and enjoy another $2,909 in regular annual depreciation for a total depreciation
deduction of $22,909 in the first year.

$20,000

+

$2,909

worth considering if you consistently
have net income from passive activities

TOTAL DEPRECIATION
DEDUCTION

100% BONUS
DEPRECIATION

ANNUAL
DEPRECIATION

Cost segregation studies may also be

=

$22,909

or a capital gain from the sale of a
rental, since losses generated by rental
properties can generally offset other
passive income or gain from the sale of
rental property.

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23

Passive Losses, Passive Activity
Limits & The Real Estate Professional Status
As a rental property owner, it’s not uncommon for your properties to produce a net
loss for tax purposes thanks to depreciation and other operating expenses.

Losses from rental property

The treatment of these losses is often misunderstood by investors for various

are considered passive losses

reasons, so we’ll spend some time here to clear up common misconceptions.

and can generally only offset

Losses from rental property are considered passive losses and can generally only

passive income.

offset passive income (i.e. income from other rental properties or another business
in which you do not materially participate, not including investments). If these
passive losses exceed your passive income, they are suspended and carried forward
indefinitely until future years, when you either have passive income or
sell a property at a gain.
This is good news because a net loss (for tax purposes) means you aren’t paying
taxes on your rental income today, even if you have positive cash flow.
Generally, the only time passive losses will offset your ordinary income from a W-2 job
or another trade or business is under one of the circumstances discussed below.

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PASSIVE ACTIVITY LIMITS
Under the passive activity limits you can
deduct up to $25,000 in passive losses
against your ordinary income (e.g. W-2
wages) if your modified adjusted gross

of all individuals for the tax year,

under any of the material participation

including the participation of indi-

tests, other than this test.

viduals who didn’t own any interest
in the activity.
3. You participated in the activity for

5. You materially participated in the
activity (other than by meeting this
fifth test) for any 5 (whether or not

income (MAGI) is $100,000 or less. This

more than 100 hours during the tax

consecutive) of the 10 immediately

deduction phases out $1 for every $2

year, and you participated at least

preceding tax years.

of MAGI above $100,000 until $150,000

as much as any other individual

when it is completely phased out. Note:

(including individuals who didn’t

these limits apply to both those filing

own any interest in the activity) for

single or married filing joint.

the year.

In addition, in order to take losses against

4. The activity is a significant participation

6. The activity is a personal service
activity in which you materially
participated for any 3 (whether or not
consecutive) preceding tax years. An
activity is a personal service

you ordinary income, you must materially

activity, and you participated in all

activity if it involves the performance

participate in the activity by meeting one

significant participation activities for

of personal services in the fields of

of the following seven tests:

more than 500 hours. A significant

health (including veterinary ser-

participation activity is any trade or

vices), law, engineering, architecture,

business activity in which you

accounting, actuarial science, per-

participated for more than 100

forming arts, consulting, or any other

hours during the year and in which

trade or business in which capital isn’t

you didn’t materially participate

a material income-producing factor.

1. You participated in the activity for
more than 500 hours.
2. Your participation was substantially
all the participation in the activity

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7. Based on all the facts and circumstances, you participated in the activity on a
regular, continuous, and substantial basis during the year.
Note: these are the same tests used to establish material participation as a real
estate professional discussed below.

EXAMPLE: MAGI & PASSIVE ACTIVITY LIMITS
Your MAGI is $100,000 for the year and your rental properties produce a net loss
of $30,000. As long as you materially participate in your rental activities you’ll be
able to deduct $25,000 of this loss against your ordinary income. The remaining
$5,000 will be carried forward.
Lets say, however, your MAGI was $125,000. In this case you can only deduct
$12,500 of the loss because each dollar over $100,000 reduced the amount you
could deduct by $0.50. If you’re MAGI was over $150,000 then you can’t deduct
any of these losses against your ordinary income and the entire $30,000 is
carried forward.

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26

THE REAL ESTATE

qualifying as a real estate professional.

at all outside of your investment activities.

That said, simply meeting the above

Note: In any year you elect to be treat-

The real estate professional status

requirements will not necessarily allow

ed as a real estate professional for tax

historically allowed real estate investors

you to deduct your rental losses against

purposes, you’ll need to keep a log of

to take unlimited rental losses against

your ordinary income. You must also

all hours worked within a real estate

their ordinary income. This has now

materially participate in the rental

trade or business.

been limited to $250,000 in losses if single

activity using the same tests mentioned

(and $500,000 if married) under the

above, but is most commonly done by

excess business loss limits introduced

electing to aggregate all your rental

by the Tax Cuts & Jobs Act.

properties as one activity and then

PROFESSIONAL STATUS

In order to qualify as a real estate
professional you must spend at least

working 500 or more hours in this
single activity per year.

TAX CUTS
& JOBS ACT CHANGE
The real estate professional

750 hours in a real estate trade or

Note that if one spouse qualifies for the

status has now been limited

business and more than half your

750 hour test, both spouse’s time on the

to $250,000 in losses if single

total working hours must be in a real

rental properties count towards material

(and $500,000 if married)

estate trade or business.

participation, and losses can then be

under the excess business

taken against either spouse’s income.

loss limits by the Tax Cuts

This is a great strategy for couples where

& Jobs Act.

Due to these requirements, many
investors who work a full-time job or
full-time in another business that is not
real estate-related will have a hard time

one spouse works in a real estate trade
or business, works only part-time, or not

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Capital Gains
Tax and Depreciation Recapture
• If you hold property for
less than a year before
selling, gains are taxed
at ordinary income
rates up to 37%
• If you hold property for
over a year, gains are
taxed at the long-term
capital gains rate of
15-20%

For many real estate investors, the

the property for over a year your gain

biggest tax bills will arrive upon the sale

will taxed at the long-term capital gains

of your property. This is especially true

rate of 15%, or 20% if your income

when all goes according to plan and

exceeds $425,801 if single or $479,001

you’re selling into a strong market while

if married.

cap rates are low. Below we discuss
what taxes you can expect to pay after

DEPRECIATION RECAPTURE

the successful sale of a property and

The dark side of depreciation is

how best to mitigate them.

depreciation recapture, which rears its

CA PITA L G A IN S TA X

claws upon sale of a depreciated asset.
Depreciation recapture is the portion

If you hold your property for less than

of your gain attributable to the depreciation

a year before selling you’ll have to pay

you took on your property during prior

tax at your ordinary income rates (up to

years of ownership, also known as

37%) on the gain. However, if you hold

accumulated depreciation.

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Depreciation recapture is taxed as
ordinary income up to a maximum
rate of 25%.

EXAMPLE: CAPITAL GAINS TAX AND DEPRECIATION RECAPTURE

N E T IN VE STM ENT I NCOM E TAX

You purchase a rental property in 2010 for $275,000 and later sell it in 2018 for

( N IIT)

$450,000. Each year your depreciation expense was $10,000 ($275,000 / 27.5) for a

You’ll also face the Net Investment
Income Tax (NIIT) of 3.8% if your income

total of $80,000 in depreciation over 8 years. This lowered your adjusted basis in the
property to $195,000 making your total gain on sale $255,000 ($450,000 - $195,000).

exceeds $200,000 if single or $250,000

The $80,000 of gain from depreciation is taxed at 25% for a total of $20,000. The

if married. It’s important to note that

remaining gain of $175,000 is taxed at the long-term capital gains rate of 15% for a

while the NIIT applies to both rental

total of $26,250. Also, because your total income was above $200,000, the entire gain

income and capital gains, those that

of $255,000 is subject to the 3.8 NIIT for a total of $9,690. When you add this all up

closely follow this guide may not report

your total tax upon sale is $55,940 or nearly 22% of the total gain. You may also be

any taxable rental income. Finally, if you

liable for state taxes, depending on your geography.

meet the requirements to be considered
a real estate professional for tax
purposes, your real estate income is
not subject to NIIT.

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MITIG ATING TAX ES UP ON SALE
As you can see from the example above, the tax upon sale can be substantial. Luckily
there are some things you can do to defer and/or reduce this tax liability.
TAX LOSS HARVESTI NG

It’s important to note that 1031
exchanges have a very strict timeline
that needs to be followed and generally
require the assistance of a qualified
intermediary (QI).

In general, capital gains can be offset by capital losses. Tax loss harvesting is simply
the selling of capital assets (e.g. stocks or other real estate) at a loss to offset your
capital gain.
This most likely makes sense if you invested in stock, rental property, or another
capital asset with a fair market value that has now fallen below its adjusted basis
(purchase price) and is unlikely to recover.

1031 Exchanges allow you to
defer both the capital gains
tax and depreciation recapture
from the sale of a property and
invest the proceeds into another

1031 E XCHANGES
1031 Exchanges allow you to defer both the capital gains tax and depreciation recapture from the sale of a property and invest the proceeds into another “like-kind”

“like-kind” property, often called
“trading up”.

property, often called “trading up”. While you ultimately have to pay tax at some
point down the line, with the notable exception of inheritance, this allows you to
use the entire proceeds to purchase a new property, thereby increasing the size of
your portfolio at a faster pace that would otherwise be possible if you were paying
capital gains taxes upon each sale.

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30

OPPORTUNI TY F UND S
Introduced by the Tax Cuts and Jobs Act, Opportunity Funds allow you defer and
reduce the capital gains tax from the sale of any capital asset. Unlike a 1031 exchange,
you only have to redeploy the capital gain, not the entire sales proceeds.

TAX CUTS
& JOBS ACT CHANGE
Opportunity Funds allow you

If you invest the capital gains in an Opportunity Fund within 180 days and hold it

to defer and reduce the capital

for 5 years you’ll reduce your original taxable capital gain tax liability by 10%.

gains tax from the sale of any

If you hold it for an additional 2 years, the original gain liability is reduced by

capital asset.

another 5%. If you then hold your investment for another 3 years, the new
capital gain from the Opportunity Fund itself becomes fully tax exempt.
In order to take full advantage of the tax benefits that Opportunity
Funds offer you’ll need to invest by December 31, 2019. That’s
because you’ll have to pay tax on the majority of the original capital
gain in 2026, regardless of whether or not you continue to hold
your investment in the fund.

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It’s important to note here that the

EXAMPLE: OPPORTUNITY FUNDS
You purchase a $100,000 property in 2010.
In 2019 you sell the property for $200,000 and roll the $100,000 capital gain into
an Opportunity Fund within 180 days. In 5 years, your taxable capital gain of
$100,000 invested in the Opportunity Fund is reduced by $10,000. And in 7 years
it is reduced by another 5%, reducing your original taxable capital gain by a
cumulative total of $15,000. This means you will only pay capital gains tax on
$85,000 of your original $100,000 gain.

tax benefit related to reductions in the
original capital gains liability is modest at
best, so rental property owners will need
to carefully weigh the pros and cons of
1031 exchanges versus Opportunity Fund
investments. It’s likely that an Opportunity
Fund investment will only be preferable
to a 1031 exchange for rental property
owners when they expect the Opportunity
Fund investment to significantly outperform

You continue to hold the investment for another 3 years. During this time,

the rental property market over the next

your $100,000 investment in the Opportunity Fund appreciates to $150,000.

10 years.

Because you held the investment for 10 years, the tax on your $50,000 gain
from the Opportunity Fund investment is completely eliminated.

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32

IN S TALLMENT SALES
An installment sale, sometimes called seller or owner financing, allows you to sell
your property to a buyer and receive payments over a predetermined number of
years. This spreads out your capital gains tax over several years and gives you an
additional return in the form of interest.

EXAMPLE: INSTALLMENT SALES
You purchase a property in 2010 for $30,000 and want to sell for $110,000 in
2018. Your AGI is $180,000 and this $80,000 capital gain will increase your AGI to
$260,000, causing you to pay an additional 3.8% net investment income tax.
Your CPA suggests selling this property using an installment sale to avoid the
3.8% tax.
You find a buyer and sell them the property for $110,000. They put $10,000 down
and finance the remaining $100,000 over a period of 10 years, plus 6% interest.
Each year, $7,273 out of the $10,000 payment is considered a capital gain and the
other $2,727 is your return of principal. You’ll pay $1,091 in capital gains tax but
no tax on the return of principal. The interest you receive will be taxed at your
ordinary tax rate and you’ll avoid the NIIT in the current year

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USIN G COST SEGREGATI ON TO O F F S ET
CAPITAL G AI NS
When you sell a property, current and suspended passive losses can be used to
offset the gain from sale. If you don’t have enough current or suspended losses to
offset this capital gain, you can purchase a new property and use a cost segregation
study to create current passive losses that can offset the gain. It’s actually not as
complicated as it sounds, so let’s explore an example.

EXAMPLE: INSTALLMENT SALES
You sell a property for a $100,000 capital gain and have no current or suspended
passive losses to help offset the gain. You decide to purchase a new property
for $500,000 and have a third-party company perform a cost segregation study.
They determine that about 20% ($100,000) of the property can be depreciated
using 100% first-year bonus depreciation.
This increase in depreciation expense causes your current losses to exceed
$100,000 and allows you to offset the entire capital gain from sale.

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34

Key Tax Issues for Short-Term Rentals
With the increasing popularity of

number of days per year, then according

short-term rentals thanks to Airbnb,

to the IRS, your vacation home is a

If you rent your primary residence

VRBO, and other vacation rental platforms,

rental property instead of a residence.

or vacation home for more than

14 Days or Less

15 days, then you must report

it’s important to understand some of
the tax issues related to owning and
operating short-term rentals.
RE N TIN G Y OUR P R I M ARY
RE SIDE N CE OR VACATI ON HOM E

If you rent out your primary residence
or vacation home for 14 days or less

your income on Schedule E of
your tax return.

throughout the year you do not have
to pay taxes on the income. Because

For the purposes of this section, we

your income isn’t taxable, you also can’t

assume you and/or your relatives stay

deduct your expenses.

at your vacation home for the greater
of 14 days a year or 10% of the days
rented. If you and/or you relatives use
the vacation home for fewer than this

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35

15 Days or More
However, your expenses are only deductible to the extent of your income.
Any remaining expenses will be carried forward to offset income from this activity

EXAMPLE: SHORT
TERM RENTAL
You have a three bedroom house and

in future years.

Renting Out a Room in Your House

rent out one of the rooms. If you rent
this room for 95 days out of the year,

If you rent out a room in your house you can deduct 100% of your rental expenses

its rental usage is about 26% (95/365).

including advertising fees, rental agency fees and commissions, insurance, cleaning,

Because you only rented ⅓ of your

depreciation, repairs and other expenses related directly to the rental of that room.

house for 26% of the year, you can

You can also deduct a portion of the expenses related to your entire home (i.e. mortgage
interest, insurance, etc.) However, these are prorated based on both how long the room
was rented and the square footage ratio of the room to the entire home.

only deduct 8.67% of the expenses
that relate to your entire home (i.e.
mortgage interest).
If the expenses related to your entire
home total $15,000 then you can only
deduct $1,300 (8.67% x $15,000).
However any direct rental expenses (i.e.
advertising fees) are 100% deductible.

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36

CON SE QUENCES OF TREATI NG Y O U R S HOR T - T ER M R EN TA L
AS A B E D & BR EAKF AST
In general your short-term rentals are reported as passive rental activities on
Schedule E of your tax return unless you provide “substantial services” to your
guests. Substantial services include services found in a hotel or bed & breakfast
such as providing meals, daily cleaning, maid services, travel arrangements,
vehicles or bikes, and other services commonly found in a hotel.
Note that merely providing light amenities like soap or towels is unlikely to rise to
the level of “substantial services” because it doesn’t make up 10-15% of the total rent
paid by your guest.
However, if you do provide substantial services to your guests, your short-term
rental activity is no longer considered a passive rental activity. Instead it is considered
an active business, reported on Schedule C, and becomes subject to the dreaded
self-employment tax of 15.3% on top of your ordinary income tax liability.

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20% Pass-Through Deduction
The Tax Cuts & Jobs Act of 2017 introduced a new 20% pass-through deduction
TAX CUTS
& JOBS ACT CHANGE

allowing certain business owners to deduct 20% of qualified business income if
your taxable income is below $157,500 if single or $315,000 if married. Should your
taxable income be above these thresholds, a complicated calculation will be used

The 20% pass-through
deduction allows certain
business owners to deduct

to determine the amount of this deduction. Luckily your tax professional or tax
software will handle that for you.

20% of qualified business

S A F E HA R B O R F OR L A N D L OR D S

income if taxable income

If you still have taxable income from your rental properties after following the strategies

is below $157,500 if single
or $315,000 if married.

explored in this guide, you may qualify for the 20% pass-through deduction under the
following safe harbor, which requires that ALL conditions are met:
•

The property is held directly by the individual or through a disregarded entity by the
individual or passthrough entity seeking the pass-through deduction (e.g. a person
who owns a single-member LLC that holds a rental property qualifies).

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38

•

•

Commercial and residential real

Rental services include advertising to

Rental property owners are generally

estate may not be part of the same

rent, negotiating and executing leases,

not required to file or send 1099s to

enterprise.

verifying tenant applications, collection

independent contractors unless you plan

of rent, daily operation and maintenance,

to take the 20% pass-through deduction,

management of the real estate,

provide substantial services to guests, or

purchase of materials, and supervision of

qualify as a real estate professional for

employees and independent contractors.

tax purposes.

Separate books and records are
maintained to reflect income and
expenses for each rental real estate
activity or enterprise (a separate
real estate enterprise may constitute
multiple properties as long as it is all
commercial or all residential).

•

employees, agents, or contractors all
count toward the 250 hours.
Note that even if your rentals don’t

Rental property owners are

meet the criteria for the above safe

generally not required to file

harbor, that doesn’t necessarily mean

or send 1099s to independent

they won’t qualify for the 20% pass-through

contractors unless you plan

You maintain contemporaneous records,

deduction. Regardless of whether your

to take the 20% pass-through

including time reports or similar

activity qualifies for the described safe

documents, regarding: a) hours of all

deduction, provide substantial

harbor, if you plan on taking this deduction,

services performed, b) description of all

services to guests, or qualify as

you’ll have to issue Form 1099 for all

services performed, c) dates on which

a real estate professional for

independent contractors to which you

such services are performed, and d)

paid over $600 during the year.

tax purposes.

250+ hours of rental services are
performed for the enterprise
(see detail below).

•

Services performed by owners or

who performed the services.

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Casualty Losses
A casualty loss is considered a “sudden,

If one of your rental properties is completely destroyed in one of the above scenarios,

unexpected or unusual event” that

the amount of the loss you can claim is equal to your adjusted basis in the property.

causes property damage or loss.
These events commonly include:
Hurricanes
Accidents
Earthquakes

If you receive a reimbursement from your insurance company for exactly the amount
of your property’s adjusted basis, then you recognize no gain or loss. If the reimbursement
is more than your adjusted basis, then you must recognize a gain. If it is less, then you
recognize a loss in the amount of the difference.
In the event of a gain, the good news is that you can avoid recognizing a gain by
simply reinvesting the proceeds into a property that is “similar or related in service

Vandalism

or use”. You have two years from the end of the tax period in which the gain was

Fires

received to find a suitable replacement.

Floods
Volcanic Eruptions
Terrorist Attacks

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EXAMPLE: CASUALTY LOSSES
Your rental property has an adjusted basis of $114,000 in 2018. A wild fire
strikes, completely destroying the property.
In Scenario A, the insurance company cuts you a check for $114,000. No loss or
gain is recognized. In Scenario B, the insurance company cuts you a check of
$126,000, the property’s fair market value (FMV). You would have to recognize
a gain of $12,000.
However, you purchase a similar replacement property that cost $126,000 in
2019. In this case, you do not have to recognize the gain, but your basis in the
new property would be $114,000, the adjusted basis of the original property.

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41

This guide should equip most rental property owners with basic tax strategies
needed to minimize next year’s tax bill. It’s also a great source of ideas and possible
scenarios to explore with your CPA. This is not an exhaustive list of all available real
estate tax strategies and there may be additional actions you can take to further
reduce your tax liability.
For more information on how the strategies discussed in this guide might apply to
your specific situation, and tax compliance in general, we recommend consulting
directly with your CPA. Also see the official guidance provided by the IRS, other tax
content developed by Stessa, and further resources available via The Real Estate CPA.

While reasonable efforts were taken to furnish accurate and up-to-date information, we do not warrant that the information contained in
and made available through this guide is 100% accurate, complete, and error-free. We assume no liability or responsibility for any errors
or omissions in this guide.

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42

Meet Stessa
AUTOMATIC TRACKING & REPORTING
FOR RENTAL OWNERS

Make tax time a breeze
Get time-saving tools that make

Save time on income
& expense tracking

reporting painless and help

Link your bank accounts to Stessa

maximize your deductions--from

and transactions update in real-time.

tax-ready financials to end-of-year

Categorize transactions into tax-ready

performance statements.

categories for easy reporting.

Get key performance

Stay organized with

metrics in one dashboard

receipt capture

View your entire portfolio in one

Keep track of and scan receipts right

streamlined report that automatically

from the phone app. Stessa automatically

calculates key metrics and provides a

reads, categorizes and stores them for

clear picture of your investments.

you - no more data entry!

Keep your data safe with

Built by rental investors

bank-grade security

for rental investors

Designed from the ground up with

Stessa was built from the ground up

multiple layers of security. Stessa

with rental investors in mind. We take

uses bank-grade encryption to keep

care of all the tedious tracking and

your financial data safe and secure.

reporting details so you don’t have to.

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43

Stessa gives the millions of real estate investors with
single-family rentals and multifamily buildings a powerful
new way to track, manage, and communicate the performance
of their real estate assets. Tracking rental property finances
and monitoring performance used to be time-consuming
and tedious. Now, Stessa’s smart income and expense
tracking technology makes it effortless, automating the
busy work and saving property owners valuable time.
Get a current view of how your portfolio is performing,
and get the insights you need to make decisions without
the manual spreadsheet updates.

How It Works
Take a few minutes to add your properties, link your bank
accounts and everything updates in real-time. To learn more
get started with a free account, go to Stessa.com.

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44

This content was created
by Stessa in partnership
with The Real Estate CPA.
Thomas Castelli, CPA is
a Tax Strategist and real
estate investor who helps
other real estate investors
keep more of their
hard-earned dollars in their pockets, and out of the government’s.
The Real Estate CPA is a 100% virtual accounting firm that
helps individual real estate investors, syndicates, and private
equity funds save thousands in taxes and grow their business
with outsourced accounting and CFO services. While traditional
CPAs will take on clients across numerous industries and
become “generalists,” we only service real estate investors or
business owners in the real estate industry. We eat, breathe,
and live real estate!

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45

Save time with tax-ready financials for all of your rental properties. Visit Stessa.com.

46



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