As @Michael Greenberg said, definitely check out the laws in your area.

I knew wholesalers definItely have ways to find them and have no problem working wIth them.

If you're part of the blended retirement system then definitely contribute to the 5% match because that is an immediate 100% return on your investment. 

Definitely some risk there.Hope this helps I know I wrote a lot and there might be some parts in there that don’t make sense but I’m doing this thing in one take. 

Another option would be to get a low money down payment loan, but then they would have to pay PMI, unless if it could be avoided somehow.Applicant 2 aloneThis applicant would definitely not qualify for good interest rates but they could comfortably put a large percentage down, e.g. 30% ,50% ,70% depending on what they are comfortable with.Applying JointlyIf both applicants apply together would they qualify for interest rates as good and what applicant 1 could get on their own?

There is still some opportunity north side of Chicago but definitely opportunity south side and south suburbs. 

I will definitely reach out to you once I get my license.

First off, semantically  speaking, your discussion lacks a definition for the word "Legal"  While there are contracts in which a breach is a punishable offense, I am assuming you mean "Legal" in the "right to seek compensation for damages" sense.   

@Scott DixonThank you I definitely appreciate that.

Thank you for the insight, I definitely wouldn't have planned tackling a rehab for a while, but I like the idea of wholetailing as well.