Have met him personally a couple times and he is just a great guy all around. 

Generally speaking, with SFR or small multis, I just rely on the lease/rent roll (and some form of proof of payment; i.e. bank statements, deposit receipts, tax returns, etc.). 

I personally would recommend the last method.

but i also 2nd @Jay Hurst's sentiments - get a 2nd or even 3rd opinion on DTI/ full doc. i personally love files that are puzzles, i get some weird satisfaction out of figuring out how to make it work on full-doc, especially when my client has been told "no" before. if it doesn't work now, a good loan professional will help you create a path forward.

Personally when buying rentals I tend to buy in neighborhoods that I feel like I wouldn't personally mind living in and when I look for tenants I try to look for people that not only pass my screening but also I personally don't dislike.  

I let the booking expire and figured it was a troll.I then get another request from the same person about a month later for the same dates.

As a disabled person, I want to be in real estate, but I know I am limited. 

Essentially the Fund would be our bank that lends to my LLC who purchases the properties.

Personally I would not.

If someone is walking down the street and trips on your sidewalk or a  walk way whether its a tenant, delivery person or passerby you are the one who gets sued because its premises liability exposure.