Hi @Jacob Dalton,Thanks for sharing your situation—it’s clear you’ve put a lot of thought into this decision, and I can understand why you’re concerned given the challenges of being a landlord in Cook County.Screening tenants is definitely a key step, but I agree it’s not foolproof.

As an aside, my laundry pods for the guests and liquid for the turnovers are "free and clear" and have never gotten a complaint.I have had guests break into my owner closets, but oddly never steal (they were kids probably looking for liquor). 

But anyone who considers themselves a GC for hire, it's a bit odd they wouldn't first get their ducks in a row, it's quite easy.If it was me, I wouldn't worry about him not being licensed/insured, I would just make sure to vet him.

The GC does a lot of the odds and ends work of tying the place together.

Fun example: my business partner had an STR in Sedona with an oddly long laundry room. 

It is extremely odd the previous companies did not ask for that if they are collecting rent for you and issuing you disbursements.  

If everyone took the cash for keys approach, then the odds of a LL getting such a tenant increases.I have never had to do a cash for keys.  

Before investing here I suggest you read The Ultimate Guide to Grading Cleveland Neighborhoods to get yourself an understanding on the market.

That seems odd to me. 

That truly determines the successful from the unsuccessful, making it happen despite all the odds against you.I have a similar story of finding real estate and achieving financial freedom over the course of 4 years, going from 0 to over 300 doors.