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Miami - Awful climate, crime, no positive attributes at all
NYC - Too crowded, too much of an ego, overpriced
New Orleans - I don't care for the culture, terrible climate, run down
San Francisco - Painfully liberal, ridiculously expensive, dirty
Oakland - SF with more drugs, crime, and poverty
Whole lotta hatin' goin' on. Given the right opportunities, I think I could be happy in any city in this country of increasingly spoiled children.
All things being equal, my less preferred cities would be those where prolonged exposure to the natural elements would hasten my death many months out of the year, where the place known as "outside" becomes something to be avoided. Most every other variable in a city experience can be managed effectively according to your own priorities if you make the right decisions.
Also re: Chi being nicer and more fun than NYC... eh, I disagree. NYC is on another level than Chicago, Chicago is great and has it's advantages, but I will still concede to NYC, and so should everybody else unless they have some warped bias.
Walk through downtown Pittsburgh, and compare that to downtown Jacksonville. Your opinion on how "dying" or "dead" Pittsburgh is will change.
I'm going off of fact, not opinion. Just look at the statistics. Pittsburgh is dying.
Also, leave Jacksonville out of it. We might have a "dead" core but we have one of the best neighborhoods in the country, the oldest city in the country less than an hour away, one of the best rivers in the country, world class beaches that any city would want, and... a GROWING population (-> #40 Table of United States Metropolitan Statistical Areas - Wikipedia, the free encyclopedia)!
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