The Market Is Uncertain. Your Tax Bill Isn't. Why We're Buying Property Number Eight Now. episode artwork

EPISODE · Apr 24, 2026 · 21 MIN

The Market Is Uncertain. Your Tax Bill Isn't. Why We're Buying Property Number Eight Now.

from STR Like The Best · host Michael Chang

There's always a reason not to buy. In 2020 it was COVID. In 2022 it was rising rates. Today it's tariffs, gas prices, and AI uncertainty. The investors who waited are still waiting.In this episode, I sit down with Liz to walk through exactly why we're closing on our eighth short-term rental, a $2.1M property, despite everything happening in the headlines right now.We're not ignoring the noise. We're explaining how we filter it, why the STR tax loophole makes buying now more compelling than ever, and how being a married couple investing together is one of the most underrated advantages in real estate.We break down:Why there's always a reason not to buy, and why waiting has cost investors more than any recessionThe exact data process Liz uses to find underserved markets and identify the right propertyHow the 100-hour rule works as a married couple and why your combined hours are more powerful than you thinkWhy we pushed closing back 10 days on this deal and what the due diligence process actually looks likeThe basis step-up strategy we're using to pass this portfolio to our kids tax-freeWhy the One Big Beautiful Bill has made STR assets more valuable than they were a year agoThe bottom line: uncertainty is permanent. Your tax bill is optional.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 Apr 24, 2026

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There's always a reason not to buy. In 2020 it was COVID. In 2022 it was rising rates. Today it's tariffs, gas prices, and AI uncertainty. The investors who waited are still waiting. In this episode, I sit down with Liz to walk through exactly why we're closing on our eighth short-term rental, a $2.1M property, despite everything happening in the headlines right now. We're not ignoring the noise. We're explaining how we filter it, why the STR tax loophole makes buying now more compelling than...

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The Market Is Uncertain. Your Tax Bill Isn't. Why We're Buying Property Number Eight Now.

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This episode was published on April 24, 2026.

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