I'm not sure which places are best to focus on with rules and regulations getting strict in some places. 

If in the rare chance they do allow short term rentals in the HOA rules/regulations and association documents, don't be surprised if they change that ruling after you buy. 

It's his niche, but I think he is very helpful for people who know nothing about international investing because there are some good overviews of the viability of the markets and regulations of STR.

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

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

It is a federal regulation but some states reach out and screw you.

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

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.

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

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!