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I'll go with Boston, but would take both in a heartbeat. It's by the ocean though, has fantastic architecture (I know Chicago does too), and still great transit and the crime isn't as bad/isn't as ghetto looking.
Ft Collins because its a way more convenient location and also larger.
Ketchikan, AK or East St Louis, MO
This one's hard. I assume by E. St. Louis you mean Illinois. Illinois outside of Chicago is probably one of the most depressing states I have ever been in, and there's really not much to look at. E. St. Louis has St. Louis nearby, but I wouldn't be living there. Ketchikan is isolated, but beautiful. I would take Ketchikan if I had to choose.
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