I have some cash, but likely not enough to fund a purchase without bank financing, and especially not when factoring extensive rehab costs into the equation (may need to up my knowledge on creative financing to bridge this).

The repair was extensive and costly, requiring excavation (about 3x6 feet) to replace the broken section and clean up the mess.

Cozy was "good enough" for awhile but the lack of a mobile app and multiple tenants having issues setting up payments, etc caused me to look elsewhere.  

This would apply to your unit.Your biggest concern with setting the rent should be the near future. 1) Your insurance is guaranteed to go up, probably dramatically.  2) You may get an insurance assessment bill to cover the CA Fair Plan losses.

You could also list low and if the demand is really there, could get bid up.

The biggest reason I would advocate for mixed use is for the reasons you mentioned, the leases are longer, but also the general "issues" around tenants on the residential side don't come into play as much or at all. 

These cities literally helped build up this country and our economy and I will never understand how much negativity they receive for fighting through adversity and playing the cards they're dealt!

Post the notice as soon as they violate the lease and it should come from a lawyer not you.

One of the benefits is that being on the loan can help build his credit, which will be valuable for his future financial goals.

This is a question that has come up a million times and will continue coming up forever in Chicago unless eventually things change one way or another.