I loaded up 40 square of gray double lap , and 22 square of white vinyl siding , j channel ,corners ,every last box in the pile  ...............................For free .      

I would say allow at least 10% over what your budget is as a safety net.I don't know anyone that bought a property and didn't have to put something into it the first year.Also a red flag is when the agent who knows the area says it's tough to find tenants. 

(I'm pretty sure he has a substance abuse issue)If he were to quit claim the house to her so she had 100% ownership would that raise any red flags with the title or potentially interfere with my deal when we go to close?

Although, Chicago's dynamics are very different from Detroit but this does raise red-flags.

Best of luck hope you get that squared away!

The concern with the theoretical one year (as used in your example) when we chose to join forces, one of us is going to have been more or less invested than the other in terms of costs, time, etc...no two properties are going to perform/require management identically and it will be a hassle to try to square expenses up when we aren't just operating from a joint account under our company name.  

If your payment is 580, that leaves you 170 to cover the rest which will put you in the red my friend.

The building would be in my name.The building sit's on a town square.

Paint the door a red (close to the shutters) or navy blue.

If the hard money folks you are in touch with dont have one ......RED FLAG