Southside of Chicago? A wasteland if I ever saw one. Lived in Chicago and traveled through for many years on my way to family in Wisconsin. My greatest fear was breaking down on the south side of Chicago, anywhere between Gary, IN and the Loop. Back in the day I knew the city pretty good. God bless you for making a positive impact in a very struggling area.
I used to live in the far south side neighborhood of Hegewisch, where Chicago ends. It was okay — gritty and blue-collar, but not shot to hell like most of the south side is. I am now in northwest Indiana — better, but still a wasteland politically. I see a few positive signs - the two old ladies who run the hardware store in Hegewisch always have conservative talk on the radio, and I have seen a few Gadsden flags flying.