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Short Term Rental Riches

Jul 12, 2022

What if you could travel for free? Without tax that is. Well, you likely can.


I stayed at the most remote Airbnb I’ve ever stayed at in my life. I literally could barely get to it. After putting the jeep in 4x4 and dredging up and down muddy roads with deep crater-like holes we finally made it. Not without, however, two gracious Colombian gentlemen helping to push us up a hill while I had the throttle to the floor and mud shot all over their ponchos.

It’s hard to imagine a moment of peace after such an arrival. But it was peaceful. Staring out at the beautiful mountains where the clouds rolled by like waves in the sky. The rain spattered in from time to time but there was no noise to be washed out. Just the sound of nature and a crisp breeze.

Of course, as an investor in the short-term rental space, having accommodated over 20,000 guests in my properties, my mind started churning. I couldn’t help but think about the future success (or failure) of this property. Was the arrival just too treacherous? Was this property just too remote? We’ll break down the pros and cons of remote listings this week and wrap up with just how cool it is to explore the world and travel tax-free! This week's topics: 


  • Remote properties
  • Pros and cons of operating remote properties 
  • Expectations
  • Are you eligible for a tax write-off for travel? 
  • Is it possible you could use travel expenses to offset your ordinary income? 


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