Bought the rentals first and thinking about tax strategy second? You’re not behind.

In this episode of the Hidden Money Podcast, CPAs Mike Pine and Kevin Schneider continue the short-term rental series by answering a question they hear constantly: “I already own rentals… did I miss my chance?”

They explain why material participation is tested year-by-year, how investors can potentially use cost segregation and catch-up depreciation after the fact, and why many people are unknowingly leaving “chips on the table” even if they’ve owned properties for years.

They also tackle the biggest fear around accelerated depreciation, depreciation recapture, and walk through several ways investors plan around it (including 1031 exchanges, tax planning in the year of sale, and opportunity zone strategies). Plus, they break down why high-income W-2 earners may need different timing due to excess business loss limits.

If you’ve been told “there’s nothing you can do,” this episode will show you why that answer is often wrong and what to explore next.

Schedule a consultation today: RevoTaxpayer.com

Material participation is the make-or-break rule behind the short-term rental tax strategy... and the first thing the IRS looks at in an audit.

In this episode of the Hidden Money Podcast, CPAs Mike Pine and Kevin Schneider explain what “material participation” actually means, why it determines whether STR losses can legally offset W-2 or business income, and how to document your involvement in a way that holds up under scrutiny. They break down the key IRS tests (including the 500-hour safe harbor and the 100-hour “more than anyone else” rule), what counts as participation, and the common mistakes that cause taxpayers to lose the deduction or create bigger problems than they expected.

If you’re a short-term rental investor, high-income earner, or business owner using real estate for tax strategy, this episode will help you protect the benefit and stay on the right side of the rules.

In this episode, we cover:

• Why material participation is the cornerstone of STR audit defense

• The IRS tests that determine active vs. passive treatment

• How to build proof with time logs, calendars, texts, and emails

• Why reconstructed or “too perfect” logs can backfire

• Practical steps to track participation without overcomplicating it

Want help building a defensible strategy? Get a free consultation at https://www.revotaxpayer.com/

Most short-term rental buyers assume they need 20–25% down and a traditional investment loan. But what if that assumption is costing you deals, cash flow, and tax leverage?

In this episode of the Hidden Money Podcast, Mike and Kevin sit down with STR lending expert Jeff Chisum to break down how short-term rental financing really works including the 10% down second-home loan strategy many investors overlook.

They unpack how the right financing structure can dramatically improve cash-on-cash returns, how tax strategy and lending strategy must work together, and why “expensing everything” on your tax return can actually hurt your ability to qualify for future loans.

If you’re buying your first Airbnb or scaling a short-term rental portfolio, this episode could change how you think about funding your next property.

In this episode, you’ll learn:

• How 10% down STR loans work

• Second home vs investment property loan differences

• Why some CPAs accidentally hurt lending approval

• How depreciation affects loan qualification

• How smart investors scale STR portfolios

Hidden Money isn’t about risky loopholes, it’s about understanding the rules and using them strategically.

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