I do a procedure every year at tax preparation time. 

We would greatly appreciate your guidance regarding any requirements, limitations, or recommended procedures in this context.

Research local regulations thoroughly, as towns often require permits, owner occupancy, or restrict rental days.

Hey @Caprice Watkins, so Sheboygan does have some STR regulations. 

Buying in those areas makes more sense for STRs as the municipalities rely on the revenue.Less chance of a lot of regulation.

Likely they will only allow you to live in the property once you refinance out of the debt due to rules and regulations, but you can always ask! 

Part of this is regulations in my city, but after having done it this way, I wouldn't ever want to do it with a single family home.

As an appraiser I’ve appraised a handful of properties recently that are outside of city limits and operating successfully as STR’s that don’t have the same regulations as the city of St Pete.

However, since market shift / rate increase even these guys have slowed down quite a bit.Regarding regulation, I think eventually Indy will have to regulate against Short Term Rentals.

However, too many risks with that, and too many regulations I guess...