If you are staying in an a place for 2+ months, you don't care as much what it looks like, you care that it is comfortable and functional.

If you aren't comfortable with assignment fees, then don't work with wholesalers. 

I'm also happy I bought this in all cash as the anxiety of having to shell out loan payments on a property that isn't anywhere close to ready to producing an income (I'm not comfortable renting until this problem is fixed) would have put me in a very bad mental state - and now that I think of it, a bank probably wouldn't have approved a loan with this problem anyway.

A lot of conventional lenders/underwriters are not comfortable with rental property, so you might interview a few other lenders if you plan to really scale up your processes. 

This business is built around rejection, get comfortable with it.Best of luck.

@Adam Elbary: I can't speak to conventional lender requirements, but many private/HM lenders will be comfortable with less than 25% down... as long as you are buying the property below market/appraised value.

I would try to meet the owner at the property to discuss the paperwork or a coffee shop an informal setting where they feel comfortable seems to work the best for me. 

What can I do with this money to maximize my return of the cash-out?

With that in mind, my alternatives seem to be FHA, find a partner, or just save until I feel I'm in a comfortable range to afford the DP. 

@Jeremy KerrProps for stepping out of your comfort zone.To be honest, your worth in this particular deal is whatever the experienced large scale investor thinks it is (assuming you have no finder’s fee written contract in place.)Ballpark estimate in my opinion is that finding the deal might be worth 5% to 10% of the deal pending structure of the deal.If the large scale investor is a person of character and integrity, he should provide some form of compensation given your relationship with this person.My suggestion would be to not focus on the compensation per se but try to learn as much as you can from this person during the evaluation of the deal.