We're an instant gratification world. 

The only part of the transaction you may have to use your own money is for the EMD - Earnest Money Deposit - to give to the original seller.

Or does it make sense because there's significant value add and 20k in instant equity?

Credit scores would support what I'm looking for without additional co-signer,, one thing you need to consider is that if you permit co-signers it sets a precedent. and Fair housing could be made a thing unless you only require co-signers for students,, but they are graduating so no longer students.. so wouldn't qualify as eligible for co-signer..I don't believe in co-signers I rather have extra on deposit. 

I have one property manager that has her own crew and does a little bit of the same thing - I put a deposit down on painting and then trued it up with her a couple of months later.  

The capping of security deposits, and the "Payment Plan" of the security deposit.Payment Plans Required –Landlords must allow an installment plan to pay a security deposit, a pet deposit, move-in fees, and last month’s rent.

If successful you don't like it you lose a deposit. 

Benefits:  If they move, you KEEP THAT DEPOSIT.  

Portland Commissioner Chloe Eudaly announced she plans to call for reform of rental housing deposit regulations and is considering:(a) limiting the deposit amount;(b) requiring that it be held in an interest-bearing account; and(c) clarifying the definition of reasonable wear and tear.In an article published in today's Portland Tribune, Eudaly claims to have set up a stakeholder committee meeting of landlords, tenants and housing advocates.

A "preliminary" closing disclosure would provide a date in their system.They will not require you to pay the full down payment if you've already paid an earnest money deposit.