We only disagree on what is basically a customer service issue.

After I did find the coverage I am getting notifications from the insurer that a long litany of minor issues must be addressed (at almost every house). 

There are cheaper one’s in D/F areas but I would be careful as those can create a laundry list of additional issues.

Your biggest issue is that $50k may not let you get a nice house and have any reserves.

Flat out, I realize we're friends/family, but I need this lease in place to comply with laws that require things in writing and for my protection should there ever be issues.

Sometimes, unseen issues (like major repairs) end up costing more than the discount you negotiated.Final Thoughts•If there are no major rental restrictions, and the numbers work based on rental comps, this could be a great first investment.

You have to pay fees, but you'll have a professional handling issues instead of bleeding money trying to figure it out for yourself, then you have your time free to pursue other things.

The south and west sides of Chicago have historically had a lot of issues, and many investors have done well there.

I had a similr issue a few years ago with a property in Cleveland where my property manager hit the same roadblock.

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.