Can't help much, I've made it a rule to try to swing wide around the city because it's congested all day every day.
Try posting under Illinois, Chicago. My only trip through the near South side was in about 1970 and if you've seen the South Bronx of NYC you know it's very similar.
We were sent to pick up the wine for a golf tournament sponsored by an Italian social organization with origins in Sicily. We were armed but told to hide the guns under our seats when we reached the loading dock of our destination.
Big concrete building with no windows and no shrubs on the wide encircling lawn. The people inside were far more scary than the folks in that neighborhood. That's not to say I would move there unless I knew specific good neighborhoods.
DON'T TRUST YOUR REALTOR
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I'll believe corporations are persons when Texas executes one.: LBJ's Ghost
What's important to you? Location, commute time to the city, school programs, types of homes, price range & size? A lot of time budget is a big part of the decision - the homes in the south suburbs are usually pretty good size for the buck!
Three story brownstones were selling in bad sections of Reading PA for 10K not long ago. No secure parking and increaed drug use may have destroyed the effort by now.
I think gentrification fares best in areas with rich histories and usually near freeways.
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I'll believe corporations are persons when Texas executes one.: LBJ's Ghost