[the urban politician]

There are small condo buildings like yours that are actually marketing themselves as conversions. There is one that I was aware of a few months ago in the Humboldt Park area, I believe. Probably 2/3 of the units were owner occupied and many of the owners were interested in a leaseback.

One of the reasons this is appealing is that owners tend to take better care of their places than renters. So you can buy into a building that is otherwise well maintained and probably doesn't need any money put into a rehab. All that really needs to get done is a bunch of legal maneuvering to convert back to a rental, which includes combining all of the PINs which usually reduces the property taxes.