Get on plane and engage all 5 senses though. 10 years from now, it probably  won't really matter.

It is increasingly more difficult to pay of even one mortgage when you are cashflow negative, let alone multiple.

if your asking me Joe  I suspect wrapping a DSCR loan would be an event of default with those lenders.. and one would risk having the loan called and a lot of times if you have multiple loans with the lender they can call them all in default..

You have engaged and paid securities attorney and are compliant with Reg D offering 

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. 

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.