This gives much better diversification protection across geographies, asset types, strategies, investment subclasses etc. versus putting all the eggs into one basket.The downside is that it's not for everyone, and a person has to be comfortable with turning over control to someone else.

Does the insurance company feel comfortable insuring in that area, does the lender want to lend on this property... and so on. 

I'm definitely out of my comfort zone and I'm afraid to take the first step. 

But be sure you find one that is comfortable working in the details of your target market.

But, I'm completely financially free and can live comfortably.

No Can Google/research provide you with the safe and comfortable environment and network in a journey that gets overwhelming and lonely?

If you’re not comfortable with your analysis and still want to pursue the purchase, I would recommend engaging the services of a real estate consultant holding the CRE designation and paying them for a short form report.   

They both have some more strict STR regulations than I would be comfortable with.

You would be violating the law for doing that.Be comforted that most prospective residents don't provide proper ESA documentation. 

I have comfort that their legal team checked off the necessary boxes.