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Totally subjective but these are for me and my tastes/preferences.
1. Los Angeles -- I completely understand why many people hate it but it's my favorite. Almost perfect weather, the ocean, the mountains, the polycentric nature of the city. So many cool areas -- Venice/Santa Monica, Silverlake, Los Feliz DTLA, Long Beach, Koreatown, and of course West Hollywood. Very creative and diverse, people come here to search their dreams. You have to drive everywhere, and traffic is horrible, but planning ahead, taking side streets, and using a sunroof help big time. Not sure if I would enjoy it as much if I had to live here and drive every day, but for vacation that's totally fine. Given how busy I am with work, school, and day to day life responsibilities, I probably realistically enjoy the amenities of LA as much as I possibly can even though I don't live there.
2. New York -- Wow! So big, alive, truly a 24 hour city. Soooo diverse and international. So many languages spoken all over the place at all times. Great areas such as Hell's Kitchen, East Village, Greenwich Village, and that's barely scratching the surface. Really need to get back here a lot more!
3. Chicago -- theoretically should be higher on my list because it has so many great things going for it, and almost everything I want in a city, but something seems off and I can't place it higher than here (maybe it's because I've lived here for so long and am getting burned out of it). Great waterfront location (though not an ocean, the lake passes), dense, diverse, walkable. Strong public transportation. Great gay scene. Solid creative scene. With the combination of a core mass of jobs/careers, along with a reasonable cost of living, is perhaps the most practical/economically sensible option on my list. Outstanding air traveling access to the entire country -- a conversation about the horrors of Chicago winters is incomplete without a mention of O'Hare and Midway. City has a longstanding major crime/segregation problem, but at least there are people seriously working for a solution.
4. Columbia, MO -- going to throw a small city in here as the post stipulated 50,000 minimum population. Columbia gets this because of its amazing True/False Film Festival, which focuses exclusively on documentaries, and its surprisingly vibrant creative scene. It is a college town, but the downtown and its university flow together in a very alive, and walkable manner. The downtown is mostly reserved for local stores/restaurants, and the chains are located on the periphery of the city. Surprisingly diverse, as the journalism school draws worldwide. No traffic problems at all. A Columbia MO resident has access to 5 million people worth of standard American metropolitan area amenities, located in Kansas City and St. Louis, as the exurbs of each are approximately 1 to 1/2 hours away. Lake of the Ozarks activities are also only an hour away.
5. Three way tie between San Diego, Miami, and Honolulu. Similar themes here -- oceans and beaches, but each presents them just a little bit differently. A 3 day weekend in winter in South Beach is a great getaway for me. San Diego is surprisingly fun -- the beaches are so scenic and Hillcrest is very fun. Honolulu is just very scenic and beautiful on an island.
Honorable mention: San Francisco
City that surprises me as to how good it is: Philadelphia
Los Angeles-To live if I could afford it,, lol
Philly-To live /burbs only
Nashville-To live
Miami / on the fence as far as living
Las Vegas- Could live
12 Honorable mention's I had to list,,, sorry couldn't help my self, I like them too!!
San Francisco-Could live
Chicago-Could live burbs only
NY- Visit only
Memphis - Visit only
Dallas -Could live
Houston -Could live
San Antonio -Could live
Louisville -Could live
Baltimore-Could live/Burbs only
DC -Could live/ Burbs only
Knoxville-Could live /Nice to visit
Chattanooga-Could live /Nice to visit
Living in Baltimore, I plan to explore Philly soon. From what I've read I will consider it for my next move (though I've only been once and obviously have a lot to learn)
Location: Miami (prev. NY, Atlanta, SF, OC and San Diego)
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NYC
Miami
Chicago
SF
New Orleans
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