Also, regarding Chicago section 8. I've heard from numerous different people in Chicago, landlords, real estate agents, etc, that the section 8 renters are the pickiest and choosiest group of renters they see. They are always apparently (according to those agents and landlords) looking for the fanciest apartments, with the best views and nicest amenities. They know their rent is being subsidized, and they're only paying maybe a few hundred$/month out of their own pockets, so they want only the very best apartments, of course.
I know of an investor who bought a house in a rougher neighborhood in chicago, and fixed it up intending to rent it. The problem was that the investor only did medium level rehab, so that the house matched or slightly exceeded the other houses in that immediate area in quality (in terms of interior and exterior quality). The investor's logic was: why over-improve the house? Why make the interior so fancy that no one in this neighborhood can afford to live there? Anyway, Once the investor finished the moderate rehab job and tried to rent the house, there were NO takers!! For months!! Nothing was wrong with the house at all. The investor finally learned that the house wasn't nice enough for the average section 8 family, which is the type of family the investor intended to serve by rehabbing this house in the first place. The investor learned that section 8 renters are, to put it one way, kinda "snobby" when it comes to choosing the house/apartment they want to rent.
