How did you go about getting a sufficient contract that can help me get started?

@Dana PowellIf you have home owner’s insurance and require roommates to get renter’s insurance that should be sufficient I believe.

Offer to upgrade the AC in exchange for a sufficient increase in rent to pay for it.

However, if He doesn't have sufficient income to qualify - there aren't any banks that will lend him the money. 

It is up to the Trustee to determine if your offer price is sufficient, that requires an appraisal, and the Trustee has to assure the court that they have not given you preferential treatment.

We keep separate income/expense records on each property in Excel, which is sufficient for tax purposes.

Tenant placing rent monies in the mail is not sufficient for rent to be considered paid.Basically, I want them to pay with Cozy and expect they will. 

You might be able to improve that rate a tad bit using one of the newer residential mortgage programs that base it purely on the property's own cashflow (some of them will go as low as 1.1 DSCR whereas pure commercial wants 1.25), but the improvement wouldn't be sufficient so as to be worth the hassle/fees/costs/etc, knowing that you're just going to be doing it again in a year or two when you have sufficient 1099 longevity to get a Fannie loan.

I've found that Arizona, Texas and most mid-west states give both good cash flow for rentals and sufficient appreciation for fix & flips.

@Jimmy Solano, although you "really like / prefer the 14 unit property", I'm not convinced that "its lower asking price" is sufficient enough reason.