Since you're investing from a distance, I recommend interviewing multiple agents, lenders, property managers, contractors, and other professionals to build a strong and reliable team.

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?

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. 

This is a complicated situation with multiple layers to consider, so here’s my take based on your questions:If you’re looking to move assets from the partnership into individual LP (Limited Partner) names while avoiding capital gains, you’ll need a strategy that complies with tax regulations.

I say it is the first deal because it was brought to me by the owner before placing any other deals under contract (which I have done in multiple states) legally, and ethically.

I also have multiple streams of income and the ability to reduce my expenses sharply if needed to payoff a major unexpected expense.

And my property taxes and probably repair expenses would skyrocket owning multiple OOS properties or an apartment complex in an unknown market 2000 miles away. 

One system one login, multiple providers using the same platform.

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.

I hadn’t thought about the risk of expanding my portfolio by having multiple properties over leveraged, although that seems to be a growth strategy that many use,  I’m not sure it’s one I’m comfortable with.