I want to ensure I’m doing this the right way while keeping my finances organized and compliant with any regulations.

Tell him you'll give him a call :) This is one of the reasons why we tell tenants they need to vacate the property for any major repairs.  

You sound very organized for a first-time flipper so it looks like finding that mentor is paying off.

ALL of my major problem tenants happened to have had a average (adults in the household) score below 625. 

I found this article that allows Fannie Mae and Freddie Mac loans to move the loan to an LLC: https://servicing-guide.fanniemae.com/THE-SERVICING-GUIDE/Pa...as long as I am the majority owner in the LLC. 

I put a lot of time into listing and title, so likely good there.For amenties, I do have some of the major ones referenced - hot tub, Wifi, and stocked kitchen.

I have my own designs and after uploading them and sending them out for a few rounds of marketing I eventually received some un-deliverables and they were barely legible along with their being major defects during printing.

Besides frozen pipes in the winter, there's also sump pumps that if not running, could flood a basement and cause major mold damage. 

There's other dialers out there that's more custom tailored to organizing calls, lead follow-up plus much more cost effective and honest with a live customer service line.

All the cheap properties are MAJOR fixer-uppers with no Rent Zestimates - probably because there are not enough rental data points.This one is priced at $135k with only $1,152 Rent Zestimate.