I don't want to see you bank on having multiple un-related renters and have your plan fall through in the first few days. 

Because you gotta have multiple exit strategies. 

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

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. 

She lacks the understanding that there are multiple GP partners involved in larger sized deals.

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

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

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.

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.