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?

The end goal is to have a piece of land with multiple houses: one for my growing family but also a home for my mother in law.My mother in law has agreed to foot the money on a new property/land up front and when ready we can buy land from her to build/develop etc. 

I should have driven this hood at multiple hours of the day before I bought.

I’ve owned multiple mobile home parks and would never try to rent them out for the reason mentioned above.

Case in point, just today BAM announced the sale of an asset. 17.4% IRR and a 2.63 Equity Multiple to investors.

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. 

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.

Does again with multiple houses will give you $20k+/month.  

I actually asked in writing multiple times to verify it was a triplex as that is what I was wanting to buy.

I like not worrying about being sued even when the local 2-bit lawyer tells me he is going to sue me (which he has done multiple times).