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).

While they are the obvious ones, they are much less impactful to building a solid partnership.

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

@Jeff SkinnerRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

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

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?

Part 1 - https://mirrorindy.org/broken-housing-iha-indianapolis-secti...Part 2 -https://mirrorindy.org/broken-housing-indianapolis-iha-hud-s...I have spoken to multiple investors from OOS and local about section 8 throughout the years.

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.