I purchase the land from a local jeweler who I tracked down at his business and asked he was interested in selling.

I've been toying with the idea of adding an ISA to my sales business.

There is no other local affordable housing in the area.

Join your local REIA to know more.etc etc etc.   

Also, they are local to me.

Don't quote me on that, but it's easy to look up the IRS regulations.I recently had a conversation with somebody else who is planning to start an STR business. 

Just my personal opinion - get a mentor or a person who already has good experience running STR business, preferably in your area (but not 100% required). 

The founder appears to have been involved in businesses outside of real estate: ‘My dream is a locally made grooming products business’ | People | nashvillepost.comSo it does not appear there is a lot of track record there, but those are questions I would ask.

I'm going off the understanding that you still need to spend 500+ hours in the business to achieve material participation (please correct me if I'm wrong). 

Natural disasters can devastate your property and the surrounding community, leading to job losses and the closure of shops and businesses.