There are three cities I would consider moving to:
1) New York, specifically Brooklyn.
Why New York?
Everything, literally. New York has every kind of everything. The diversity is amazing. I would never be bored. A lot of my friends are there. Most of them make me feel like there is no other place in the world that could possibly be cooler or more exciting. I loved it here. If I could find a job, my career potential would be limitless. It could be a lot of fun. Also, SUBWAYS = great public transportation (a concept I am very fond of).
Why Not New York?
Dirty, expensive, stressful. I'm not going to lie and say New York didn't stress me out a bit. You have to be on your toes constantly. It's also very expensive, and I think I would miss trees/greenery/fresh smelling air a lot.
The low-down: Reality is, if I got a job there I would probably try it. But more and more I realize that I don't think I'm willing to quit my job and go there with nothing. I have weird feelings about the fact that all my friends want to go there, and that maybe I'm just getting sucked into the hype and ignoring the fact that I might be interested in being somewhere else. This is a tough one for me.
2) Austin, TX
(okay, Austin and Portland are kind of funny since I've never been to either place)
Live music scene (if you don't know me, then you must be made aware that I'm a music fanatic). Bike culture. Seemingly active and healthy culture. Mexican food. People seem happy. I could probably get a job there with the company I currently work for. My aunt's family lives 2 hours away (it would be nice to be close to SOME family for holidays and such). It's generally a young city that I hear nothing but good things about.
Why not Austin?
I think I would eventually miss seasons, especially fall. It's in Texas, which has always been a state that annoyed me on a multitude of levels. Not a great public transportation system. No friends are there.
I need to visit. There is really no way to know if I like it without ever having been there. I like the bike culture thing. I really don't like the poor public transportation system thing. I love warm weather, it makes me happy. However, I'm not sure if I can get up the nerve to move someplace where I literally don't know anyone.
3) Portland, OR
I'm pretty sure Portland is going to be my favorite city hands-down, and again, I've never even been there. I LOVE how green it is (literally and environmentally). The bike culture is amazing. The public transportation is rad. It's close to mountains and the ocean. It's seemingly full of young, interesting people, good restaurants, and culture. It seems safe, peaceful, and generally beautiful.
Why Not Portland?
I haven't heard anything too special about the job market. It's far from my family/friends, and I don't know anyone there. It's also apparently expensive, and I've heard it rains a lot, which can be depressing.
The low-down: I need to visit, however visiting could potentially be a very expensive endeavor. I could probably get a job there through my company. But it's very far, and very expensive. Yet somehow, Portland remains my favorite on this list.
In general, this is a very confusing topic for me. I'm trying to do some soul searching, and maybe try to travel to Austin and Portland to see if they're really how I'm imagining them to be. The trouble is that all of the money I use for travel could be going towards starting a new life in one of the aforementioned cities. Very difficult decisions.
***UPDATE*** After reading this over a few times, and reading quite a few forums on Austin and Portland, I feel that New York is the best place for right now. It's all I've been thinking about since I visited July 4th and I've been pursuing finding a job there pretty hardcore for the past month. Marchons, marchons!