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It turns out I kind of hate managing Short-Term Rentals.

Breezy beach condos, cozy mountain cabins, and piles of money flooding in. This is the “HGTV” image of Short-Term Rentals (STRs) - and who wouldn’t be drawn in by that Siren Song? 🏖️ But after 2 years of self-managing our STRs, I’m hiring a property manager starting next year. Don’t get me wrong – I love real estate investing and getting huge tax deductions – but it turns out I don’t really love working in ‘hospitality’, which is what managing an STR entails. Tenants at long-term rental properties are usually thrilled if you fix problems at their units within a week; short-term rental guests demand that any issue be fixed immediately – and oh, they really shouldn’t have had to deal with any problems to begin with, so they will still demand a refund and leave a bad review. 🤦‍♀️ For the past 2 years, self-managing our STRs has made the best sense from a tax perspective (bonus depreciation!), but now that we’ve taken the big tax deductions, I had to do some soul-searching to determine whether it was still worth my time and the drain on my ego. My conclusion: Sometimes your best life isn’t just lived on a spreadsheet. I love optimizing all of my investments and tax strategies to get the best outcomes, but managing the STRs made me realize that sometimes it’s more important to balance out the lifestyle you want at the literal expense of some financial gains. I don’t regret trying it out; self-managing a STR for a year to get the high tax benefits and then turning it over to a property manager may actually be the best lifestyle vs. financial benefit strategy for many investors. Moving forward I may have fewer stories for our “Ridiculous Moments in Real Estate” section, but if I have fewer guests urgently contacting me in the middle of the night to ask me what the weather will be like at my cabin on Christmas Day (a month from now), I’m considering that a WIN. 🏆

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