I like the south side, but my experience is really limited to Bridgeport, Woodlawn, Hyde Park/Kenwood, and as a student I've only really lived in Hyde Park.
I'd just have to say that a lot of the south side is not nearly as bad as you may think. The 55/Red Line trip is more anti-hype than anything else (of course, if you're standing at the stop, waiting for the 55, fanning yourself with a stack of benjamins, you may have some trouble).
My main problem is that the areas i discuss tend to be residential deserts. They're nice, quiet, but I don't particularly want nice and quiet out of a neighborhood. Living east of the Metra tracks would be a bit different, since stuff along Cornell and east is a lot more active.
EDIT: I would prefer to live in a nearer-to-Loop location, but apartments and homes along Cornell, as I said, I wouldn't mind living in at all. Close amenities, easy transportation, just the minor inconvenience of living in the same neighborhood as my college days

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