In terms of places I've been, Sudbury easily takes the cake.
For big cities, me and my buddies did a massive U.S. road trip a few years ago(16 states in one month) and Washington D.C. was a frickin hole. The rich areas are nice, as well as the Capital area obviously. But sooo much ghetto. I was also amazed at how close the run-down areas were to the multi-million dollar estates, I'd say no more than a mile or two.
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