He's on SSDI (Social Security Disability Income) at just under $1,500 a month and he wants to do some wholesales to make some extra income.Lets say he does a deal or multiple deals and makes any assignment fee on it/them and the profit exceeds 1.5k which is higher than his disability per month.

Are you getting estimates in DD to decide?

U can explore but if you actually want to do a project like this you will need to bring in someone who is experienced and bankable.

Dan I would love to help.

that doesn't make them bad investments - i'm still buying. 

Peer-to-Peer:  Popular apps that allow anybody to pay each other. 

Or else reduce enough on price to deal with an eviction from an illegal unit.I don't know Chicago laws, but in NYC if you have an illegal unit, the tenant occupying it seems to have more rights than the owner does and doesn't have to pay rent... 

You may want to think about working with a realtor or a really good attorney to make sure you are set up correctly to start off in the best possible situation. 

Non-profit or not, it will be UW as a business...the non-profit designation doesn't eliminate the lending review, just makes the proceeds non-taxable in order to be put to charitable use.

I recommend requesting a review or a new appraisal that compares your property to similar multifamily properties in the area to ensure a more accurate valuation.