Two Managers Failed, Is It Time To Sell??

Short Term Rental Problems and Solutions · May 7, 2026 · 1h 1m · transcript

Most short-term rental deals don’t fall apart at purchase. They fall apart in operations.

In this episode, I sit down with Steven, a Pocono investor who did everything right. He spent two years searching for the right property, invested over $100,000 into improvements, and hired professional management expecting a hands-off experience. Instead, he got poor performance, bad communication, and numbers that didn’t add up.

Now he’s facing a decision a lot of owners quietly consider, fix the operation himself, or sell and move on.

I manage over 130 short-term rentals in the Poconos, and I’ve seen…