I bought and renovated a condemned property in Baltimore and it was very difficult.     

But multi families seem non-existent (in terms of him being able to house hack), partial or shared ownership schemes seem like they would be very difficult to exit, and basic SFR prices seem just so high that appreciating seems to be the main profit strategy.

Would be difficult to set up a multi member llc correctly without good legal counsel.

It's difficult because most times the firms collecting have all their fees riding on you paying this inflated amount.

Ive heard banks are wayyyyyy more difficult to deal with. 

Where FHA deals can be more difficult, I am having trouble understanding how that alone is preventing your offers from being accepted and, where inventory is very low right now, suspect the $100k approval is what is limiting your choices most of all. 

I don't know how much more difficult is it to OMI a unit w/ multiple lease holders?  

A couple of years ago we were able to snatch up foreclosures in mint condition, but now it's a bit more difficult.

It will be very difficult if not impossible for you to find financing for the project if you have never done it before.

It really is difficult; and when you throw the whole service animal thing in there it becomes a legal nightmare.