re: I am blown away with Chicago

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They have gotten themselves into big trouble with the muni bonds. Hard to see how it doesn't end with somebody getting burned bad. Luckily the influx of young, rich hipsters makes the debt servicable for now.

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Pretty much

The population of the city itself has remained steady at around 3,000,000 over the last 25 years, but it has become much wealthier. A lot of impoverished citizens moved away (some to the near suburbs, some moved to the South), and the younger, wealthier professional class has exploded here. I live not far from where Cabrini Green used to be, and it's amazing what that area looks like now - there is an uber-expensive British boarding school, an REI, brand new condos, etc, etc.

The legacy costs are what's keeping the city from exploding. I honestly think the best thing that could happen right now is the city going bankrupt (or nearly there). New York was very close to it in 1975, and it was the best thing that ever happened to NYC.