Oh wow. Great question. Hope I have enough room.
1) Honolulu, HI
Upside: beautiful weather, beautiful women, ethnically diverse, super laid-back and relaxed.
Downside: incredibly high living expenses, nepotism and cronyism rule, more of a small town feel than I’d like.
2 - tie) Atlanta, GA
Upside: near my mother and my brother, delicious Southern food readily available at all times, low cost of living.
Downside: near my mother (who views me as free labor), hot summers, terrible traffic means going anywhere is a task.
2 - tie) Washington, DC - Upside: public transportation in general and the Metro specifically, vibrant nightlife, pretty good food. Downside: hot summers AND cold winters, horrible traffic, logistical headaches when dealing with two different states and the District.
4) Gunnison, CO
Upside: rose-colored childhood memories, unimaginably safe small town, lots of outdoorsy stuff to do including skiing and free climbing.
Downside: tiny town in the Rocky Mountains, virtually no other non-white people, ice cold winters, reality never matches memories.
5) Aurora, CO
Upside: More great childhood memories, great camping and skiing within driving distance, also very safe, reasonable cost of living.
Downside: public transportation sucks outside of the city center, ice cold winters, still not very many non-white people
6) Seattle, WA
Upside: very progressive city, lots of live music all the time, decent food, especially if you like hole-in-the-wall teriyaki joints, skiing within driving distance, lots of pretty girls walking the street.
Downside: very unfriendly to newcomers, none of those girls will actually talk to you, rainy, depressing winters, harder to find a decent job than expected.
7) Jackson, MS
Upside: Traffic really isn’t that bad, decent food, especially if you like barbecue, plenty of black people around.
Downside: ignorant city in an ignorant state, oppressively hot summers, not much to do besides watch television and drink, girls are not that attractive at all.
8) Mobile, AL
Upside: fresh seafood from the Gulf, cheap as dirt living expenses, some of the Azelea Trail Maids can get it.
Downside: my father lives there, nothing to do except watch television, drink, and fish, economy is in the toilet, city layout was designed by a blind man drunk off absinthe.
Not ranked: Los Angeles, CA (not enough time to make a fair appraisal), Paris, France (not fair to compare to brutish, uncouth American cities.)