Entity Tax Strategy Series

Real Estate Investor Tax Playbook

Cost Segregation, Bonus Depreciation, and Tax Secrets for Short-Term and Long-Term Rental Owners

By AE Tax Advisors -- First Edition, 2026 -- 13 Chapters

Entity Tax Strategy Series
Real Estate Investor Tax Playbook
Cost Segregation, Bonus Depreciation, and Tax Secrets for STR & LTR Owners
AE Tax Advisors

13 Chapters of Real Estate Tax Strategy

From depreciation fundamentals to advanced investor case studies -- everything you need to minimize your real estate tax burden legally and effectively.

i

Introduction

Why real estate remains the single most tax-advantaged asset class in the Internal Revenue Code -- and how this book gives you the playbook to capture every available benefit.

1

Real Estate Tax Basics

Understanding how real estate income is taxed -- active vs passive, ordinary vs capital gains, and why structure matters from day one.

2

Rental Depreciation

How depreciation works for rental properties -- 27.5 year residential vs 39 year commercial recovery, and why straight-line depreciation leaves money on the table.

3

Short-Term Rental Benefits

The unique tax advantages of short-term rentals -- how average rental periods of 7 days or less change the passive activity classification entirely.

4

Cost Segregation

How cost segregation studies reclassify building components into 5, 7, and 15 year property for accelerated depreciation -- turning 27.5 years of deductions into Year 1.

5

Bonus Depreciation

How 100% bonus depreciation under OBBBA works, which assets qualify, and how to combine it with cost segregation for maximum first-year write-offs.

6

Passive Activity Rules

Understanding passive activity loss rules -- the $25K allowance, the $150K phase-out, and why most high-income investors see their rental losses trapped.

7

Real Estate Professional Status

Qualifying for Real Estate Professional Status -- the 750-hour test, material participation, and how REPS unlocks all passive rental losses against active income.

8

The STR Tax Loophole

The STR tax loophole explained -- how short-term rentals with material participation create non-passive losses that offset W-2 and business income without needing REPS.

9

1031 Exchanges

How 1031 like-kind exchanges defer capital gains and depreciation recapture indefinitely, and the strict timelines you must follow.

10

Opportunity Zones

Qualified Opportunity Zones -- deferring and potentially excluding capital gains through investment in designated census tracts.

11

Entity Structuring

Choosing the right entity for your rental properties -- LLCs, partnerships, S-Corps, and C-Corps, and when each structure makes sense.

12

Financing and Deductions

Mortgage interest deductions, points, loan origination costs, and other financing-related tax benefits for real estate investors.

13

Investor Case Studies

Real-world case studies showing how investors combine these strategies -- a W-2 earner using STR + cost seg, a portfolio investor using REPS, and more.

Conclusion and Action Plan

A step-by-step implementation roadmap that ties every strategy together -- your 90-day action plan to restructure, optimize, and start saving on taxes immediately.

Written for Real Estate Investors at Every Stage

Whether you own one rental or a portfolio of 50, this playbook meets you where you are and shows you the path to tax optimization.

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Rental Property Owners

Owners of residential rental properties looking to understand depreciation, deductions, and entity structuring for maximum tax efficiency.

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Airbnb and VRBO Hosts

Short-term rental operators who want to leverage the STR tax loophole, cost segregation, and material participation rules to offset active income.

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Real Estate Investors

Active and passive investors building real estate portfolios who need to understand 1031 exchanges, opportunity zones, and advanced tax planning.

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W-2 Earners Seeking Offsets

High-income W-2 professionals looking to use real estate losses -- particularly through STRs and REPS -- to offset their salaried income.

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Cost Segregation Candidates

Anyone considering a cost segregation study who wants to understand the process, qualifications, and potential tax savings before engaging a firm.

Start Saving on Real Estate Taxes Today

13 chapters of actionable tax strategy backed by the IRC, real-world case studies, and years of advisory experience.

Real Estate Investor Tax Playbook

First Edition, 2026 -- AE Tax Advisors

Coming Soon

Join the waitlist to be notified when the book launches

  • 13 comprehensive chapters covering every real estate tax strategy
  • Real-world investor case studies with actual numbers
  • Complete cost segregation and bonus depreciation walkthrough
  • STR tax loophole and REPS qualification guides
  • 1031 exchange and Opportunity Zone strategies
  • Entity structuring decision framework
  • 90-day implementation action plan
Visit AE Tax Advisors

Entity Tax Strategy Series

A comprehensive library of tax strategy guides from AE Tax Advisors -- built for business owners and investors who want to keep more of what they earn.

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The Partnership Tax Book

The definitive guide to partnership taxation, allocations, distributions, and entity structuring.

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The C-Corp Tax Book

Everything you need to know about C-Corporation tax strategy, the 21% flat rate, and entity optimization.

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Real Estate Investor Tax Playbook

Cost segregation, bonus depreciation, and tax secrets for short-term and long-term rental owners.

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The next volume in the Entity Tax Strategy Series is in development. Stay tuned.

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Need a Tax Strategy Built for You?

The book gives you the knowledge. AE Tax Advisors gives you the execution -- cost segregation studies, entity structuring, and full tax planning.