Episode Details

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.

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