I have been renting out one bedroom and sharing the bathroom for 4 years,, now I have improved my second floor with a new bathroom and renting out my second floor as Airbnb, and for now it is really great.

For instance, if there's an unresolved settling issue, you can probably see cracks in the foundation, buckling, un-level floors, un-plumb doors, etc. ...but, if everything is solid now on an old house, it'll probably remain pretty solid for the foreseeable future.

Descent painted walls, affordable flooring - read “pretty cheap tile”, a good roof, and fixtures that work.  

Replacing flooring and paint?

I laid Pergo on the main floor and it definitely helped me get a great contract.

I`m looking at a 950 sq ft ,2/1 condo ...asking is 110000, ARV looks to be about 175000.It needs flooring ,paint ,and a light bath and kitchen update.

This is the worst case scenario.You can call the city of Chicago's easy permit desk whose number is available online. or you can take a field trip to the 9th floor at city hall.  

They filed a building plan with the city, then at the sales office would sell an option to get a game room over garage with the same floor plan. 

10.25% interest-only is the floor right now and that with a lot of experience. 

You should have seen that floor when we got it :-( We had to sand every square inch of that floor by hand, yikes. but it does look cool now!