Looking to Branch into Short-Term Rentals

[Ian Bollinger]

I own several long-term rental homes in MD and have been doing some research into trying a STR. I have been looking in the Tampa, Savannah, Charleston area, doing my own research and working with a local realtor. I have come to understand these are very challenging places to find a potential Airbnb due to both local regulations and HOA/insurance guidelines. I noticed that the majority of Condos/Townhome communities were ruled out due to this. Risk Factor has been helpful for identifying flood risk for various properties. AirDNA and other similar sites label these areas as high demand for short-term rentals and I always figure it can be turned into a long-term rental if it doesn't pan out. Prices in these areas look to be double - almost triple from 2020 and I am concerned I could potentially be buying something inflated/overvalued in the 400k-600k range at the end of the boom.

I've been learning about the potential for declaring an active loss (not limited by passive 150kAGI/25k loss rule) on a STR if you carefully prove material ownership + Avg stay 7 nights or less. This strategy along with the first year bonus depreciation strategy (60% now for 2024) are quite intriguing.

Anyone have experience purchasing a rental in one of these areas recently - specifically a STR? Would love to connect!

Thank you!