I hope all this was not just for his benefit as my spouse and I were really looking to be guided by a lawyer who specialized in this.

Feel free to PM me if you have any questions and I could also send you a Chicago House Hacking guide I made earlier this year.

Inspectors on power trips and not picking.

In general, the NMLS should be your compliance/regulation guide, as it compiles tons of state-level requirements.

It looks like those loans require 20% down, and I've been guided as a sort of philosophy, to use as little down as I can do that I can deploy more capital into other projects. 

If I were 30 years younger (your age) I would look to experienced intelligent investors to help guide me.

Nashville should certainly be there - regs (but well regulated, predictable) and is the favorite trip for pretty much all SEC Schools (best city by far in SEC, drivable distance, Vanderbilt sells out typically >2/3 of the stadium to opposing fans, etc.)

Here is a guide on buying in Grenada.https://www.7thheavenpropertie...

I cant seem to find any guides to help me send my info over to resimpli vs having to type it all over again. 

Me not being an accounting guru....depreciation was a bit tricky to set up, however they have a few guides, customer support may walk you through it and searching via google will help you put the correct entries.