Yea, we did something similar - not retired yet - but loved chicago so much we bought a small condo in the loop during the down turn. We loved it....BUT the HOA's kept going up, up, and up. Pretty soon we're paying the cost of a car payment and Chicago condos have strict rules about rentals and renters rights. We found through a local attorney that there are actually businesses that teach tenants in Chicago how to squat "rent free" if any of the 21 or so renters rights get violated - we were shocked. you can look this up on line. Net is that we tried to do what you are thinking, had a string of bad tenants - even in a good building, turns out that there are flyers posted in the lobby on tenants rights. It's like a scam class that is really quite sad. Net is that we got out as long term, between HOA's and the renting mentality, it can be quite challenging. If you could somehow find a place that does not have the HOA's - Lincoln park perhaps? and could do some handy work yourself, be diligent about the renters you choose, you would have a shot. Property Managers are no help with this. They often do not execute the tenants rights process correctly which then leaves you wide open to be sued or not paid and once you get in a renter in Chicago, it can be nearly impossible to evict them. Do some research on line, call some attorneys in the area that specialize in this. I think I used Andrew Polanski who is well versed in this and really awesome. Good Luck.
