Be honest with yourself about your skill/expertise level...more people fail in this business than succeed. 

I have a split level house I'm looking at but most of the comps were single story.

A high level understanding of each can be helpful.Also, try to go for base hits rather than home runs.

The cashflow is decent as a midwest city, and there are some really nice suburbs as well.I'm mostly concerned with the future of Chicago, and if it will continue losing population, or if things are expected to reverse/ level out over time.

If you do sell, the most passive alternative out there is buying index funds (although I'm not thrilled to buy at these levels honestly). 

The floor needs to be "clean" and level or anything underneath these (although they are considered a floating floor) can eventually be felt. 

Today, we are at unprecedented levels.

The upper level of the home caught fire.

The 2015 Right to charge law requires I let Tenants hook up at their expense only id prefer to do all the electrical my way so we don't have every unit doing it differently I'm adding level 2 charging so I can charge higher rents.

Assuming you are not at that level of wealth yet, just purchase it in your name and keep it simple.Good luck on your first purchase, don't over think it!