There Is No Perfect Time to Buy (And Why Waiting Is the Most Expensive Mistake STR Investors Make) episode artwork

EPISODE · Jun 19, 2026 · 16 MIN

There Is No Perfect Time to Buy (And Why Waiting Is the Most Expensive Mistake STR Investors Make)

from STR Like The Best · host Michael Chang

You've done the research. You've looked at the markets. You've run the numbers. So why haven't you bought yet?In this episode, Michael and Liz break down the most common trap STR investors fall into: waiting for the perfect moment that never comes, and the real cost of staying on the sidelines.We cover a lot of ground here, from how to train your eye to spot an outlier property, to the mindset shift that separates investors who build wealth from those who stay stuck in the research loop.We break down:The "buy yesterday" principle and why real estate rewards action over timingHow analysis paralysis keeps smart, high-income professionals from ever pulling the triggerWhat to actually look for in a property, and how Michael spotted a misrepresented A-frame in the Catskills that no one else saw comingThe pros and cons of buying at different points in the year, and why the "wait until Q4" strategy backfires more often than notWhy the STR strategy is a real estate investment strategy first, and a tax strategy second, and what happens if you get that backwardsWhy bonus depreciation being permanent in 2025 makes getting the first one right more important than everThe bottom line: there is no perfect time, but the investors who do the work now are the ones who move fast when the right deal appears.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Episode metadata supplied by the publisher feed · Published Jun 19, 2026

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You've done the research. You've looked at the markets. You've run the numbers. So why haven't you bought yet? In this episode, Michael and Liz break down the most common trap STR investors fall into: waiting for the perfect moment that never comes, and the real cost of staying on the sidelines. We cover a lot of ground here, from how to train your eye to spot an outlier property, to the mindset shift that separates investors who build wealth from those who stay stuck in the research loop. We...

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There Is No Perfect Time to Buy (And Why Waiting Is the Most Expensive Mistake STR Investors Make)

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This episode was published on June 19, 2026.

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