But Section 8 has strict rules regarding who can be there and if they violate those rules they stand to lose their voucher.

But if rentometer is correct, then I stand to cash flow roughly $300 a month after I do some small repairs and increase rents.

As for the tenant, if you are supplying window units temporarily, they have no leg to stand on.

They are the “stand alone” units you see in hotels.

You'll learn a great deal and if you can stand the punishment, eventually, you can sell for cash and get out.

As it stands I think I will focus on repairing what I can and see how far I get with paint prep.

A few common items to be on the lookout for:  Look everywhere inside and out for peeling or missing paint and fix as necessary, test windows to make sure they open, can stay open, close, and lock (old wood windows may have problems doing this regularly or be stuck all together), review basement for any signs of standard black, non-toxic mold/standing water, make sure all stairs are cleared of tenant items (no bikes, boxes, etc.).   

Are they attached or stand alone?

Something I may want to know is where they stand or feel on investing. 

As a free standing itme, that wouldn't qualify.