The Game-Changing Tax Move That Short-Term Rental Owners Overlook | Erik Oliver

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0:00 – How Real Estate Investors “Save Like They’re Stealing”
0:38 – Meet Eric Oliver from Maven Cost Segregation
4:24 – What Is Cost Segregation? (Simple Explanation)
7:30 – Bonus Depreciation: Supercharging Your Write-Offs
10:48 – Real Example: $900k Property & Massive Deductions
13:49 – Does 100% Bonus Depreciation Change Investor Behavior?
17:35 – The “Short-Term Rental Loophole” & W2 Tax Savings
19:34 – Material Participation: How to Qualify with the IRS
25:26 – Look-Back Studies & Fixing Past Depreciation (Form 3115)
29:26 – Using an Old Condo to Offset Today’s Capital Gains

💡 What if there’s a way to slash your tax bill while building real estate wealth—without buying a single new property?
In this episode, we turn the spotlight on one of the most powerful, yet often overlooked, wealth-building tools for investors: tax strategy. Eric Oliver of Maven Cost Segregation to break down, in plain English, how cost segregation and 100% bonus depreciation can dramatically reduce your taxes—especially if you own or plan to own short-term rentals.
Eric explains how accelerated depreciation really works, what the so-called “short-term rental loophole” is (and isn’t), and why material participation and intent are key in the eyes of the IRS. Jason and Rory go even further, sharing real numbers from their own portfolio, including how they used a look-back study and a “poor man’s reverse 1031” strategy to offset a large tax bill after selling a property.
If you’ve ever thought taxes were just an unavoidable cost of investing, this episode will make you see them as a strategic wealth-building tool.



Things we discussed in this episode:



Cost segregation basics – accelerating depreciation by breaking a property into components with shorter lives.

Bonus depreciation – how 100% bonus magnifies cost segregation savings in year one.

STRs vs. LTRs – why short-term rentals can offset W2 income but long-term rentals usually can’t.

“Short-term rental loophole” – a legal, code-based strategy, not a shady trick.

Material participation – key IRS tests, especially 100 hours and more time than anyone else.

Timing a purchase – buying late in the year to more easily document material participation.

Jason & Rory’s $900k deal – large depreciation created, especially from exterior work and landscaping.

“Poor man’s reverse 1031” – using cost segregation to help offset capital gains from a property sale.

Look-back studies & Form 3115 – reclaiming missed depreciation from prior years.

Tax planning strategy – using cost segregation selectively to manage tax brackets and avoid wasting deductions.


Get in touch with ERIK:


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