Contractor – This is one I really need help from the bigger pockets community in the local area. 

There’s huge retal income potential if you nail that balance between improvements that wow tenants and improvements that merely look fancy but don’t justify higher rents.I’d also keep an eye on how your high end plan fits the local demand.

@Dan Geffen moved down there and knows the area well if you want to connect with a local investor.

I would suggest going to the find a lender tab here on bigger pockets to find a local lender who has the same products. 

I would recommend tuning into Straight Up Chicago Investor Podcast and going to local meetups. 

There are also some locally I think through the AAR, I would reach out to them but if not I am happy to help!

A good property manager can help with tenant screening, enforce lease terms, and handle evictions more efficiently if it comes to that.Require a Larger Security Deposit: Within the bounds of local regulations, a larger deposit can provide a cushion in case of damage or unpaid rent.Consider Rent Guarantee Insurance: Some companies offer insurance products that can cover lost rent in case of tenant default.

I would consider the tenant's past, as well as the condition of the unit, my local market, and other factors.

First you have to face the local municipalities & will be extremely difficult to get the zoning approved. 

@Jason Khoury I purchased my current residence, a duplex, from a local non-profit about 5 years ago.