Perhaps your #6 of repurposing commercial in to multiple small residential units is the best idea I can see in SA as it has had way too many Single Family rental homes added the last few years. 

I’ve received multiple quotes from insurance companies (mainly I would obtain the quotes myself).

I'm currently flipping properties in my backyard (SoCal) and have the liquidity to fund multiple projects.

there are multiple cities across the Midsouth that make for solid investments and you are still able to even see some cashflow even in today's environment without buying just straight up high risk properties. 

I had never heard of such a thing.. and most private flippers dont know it either So like on our subdivisions whatever LLC we own it in that LLC also has to have a developers license .. so  If you have multple subdivision going in multiple LLC you need multiple developers licenses.. where this can stymie some folks  NOT EVERYONE can qualify for a Bond.

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

I’ve worked for some group home providers where they employ a maintenance worker who handles some of these issues (usually if the have multiple homes in a specific geographic location) and I’ve worked for homes where the handiest employee fixes things and that option doesn’t always have the best outcomes.

The sooner you use a system like this, the easier it will be to keep track of it all when you have multiple properties. 

Trying to run a successful PMC is difficult but trying to run multiple companies - VR, Annual, cleaning, and landscaping is probably going to give you an aneurism.

My rentals are all over the place and on a yearly basis I make multiple and consistent visits to these places.