I personally would not invest in detroit as historically its not a appreciating market and for cash flow and I invest primarily for appreciation - I go off the location location location mantra. 

Find someone where there is a personal connection and at some point your relationship now or later can benefit the mentor.

People like to rent from a person not a 'brand', it's more personal.

So despite these laws coming into effect to help landlords and I followed instructions, I'm still screwed.

Personally, I'd go with the As-Is scenario.

Sounds like the person knew what was going on with their credit report as they have filed reports in the past. 

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

One-person rental units are in the highest demand, and co-living directly appeals to this market.

It's stronger in court if they do it, nothing personal.

I have a situation where a person I know is moving out of the country and would be looking to put their home for sale in the summer.