In this episode of The Hideaways Show: Behind the Curtain, Mike is finally back after what felt like a 12-day grind in the Gorge — we’re talking 16-hour days, nonstop tasks, and the kind of behind-the-scenes chaos most people never see when building out short-term rentals. He sits down with Jordan to unpack everything he just went through and to reflect on the real, unfiltered lessons they’ve learned while bringing these unique stays to life.
Together, they walk through the top five lessons every STR investor should know — the hard-earned kind that only come from experience. They hit on why you should never assume anything, the power of getting second opinions, and why documenting every single detail can save you thousands down the road. They dive into the importance of multiple inspections (because one is never enough) and highlight the crucial role a structural engineer plays in protecting your investment, your timeline, and your sanity. It’s real, raw, and packed with wisdom for anyone thinking about building or renovating a short-term rental.
After the deep-dive, Mike and Jordan switch gears and head into their fan-favorite segment: “Would You Book It?” This week, they break down two incredibly unique stays — an unreal skyscraper treehouse in North Carolina and a rugged, scenic hut in New Zealand that looks straight out of a travel documentary. They go back and forth on what makes these properties magical from a guest’s perspective, and what challenges (and opportunities) they present from a host’s point of view.
The result is a fun, thoughtful conversation about the charm, effort, risk, and massive reward of creating truly experiential properties. If you’re obsessed with unique stays, curious about the behind-the-scenes grind, or actively building your own STR, this episode delivers insights you won’t want to miss.
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About the show:
Join us every week for The Hideaways Show! We're the team behind The Hideaways, a collection of unique vacation rentals across the U.S. Our goal is to share our journey with you, from the challenges we've overcome to the lessons we've learned. Tune in to learn and grow with us!
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