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The one place I've never been to is the pacific northwest. I have a strange feeling that I wouldn't leave if I did go there though.
Austin would be ok, the only thing that it is missing is a beach. Which Albuquerque, Denver, Phoenix and Las Vegas are also missing. San Diego and suburban LA aren't too bad if you don't need to drive very far for anything. Miami, Key West, Orlando, Tampa, and Jacksonville have occasional bad weather, and some hot and humid summers, but it isn't bad in the winter.
Sydney would be my first international pick, and I think it will be hard to find a better place to live. It is what I judge other cities on now. It's just too bad that it is on the other side of the planet. Canadian cities like Vancouver (I haven't been there yet) might be similar, but it needs to be moved to the same latitude as Mexico and have similar weather patterns.
What all of these cities need is a way for you to feel like you belong there. A sense of community. It happened in Washington DC last week. There were 2 million people and everyone was nice and happy. It was like I was in Canada. I think Austin would win this category out of the US cities I listed. Maybe it was the people I was traveling with, but I felt like I fit in there and had fun going to the dirt race track, bars, and some other places.
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