I'm not a city person, but if there's one city I wouldn't mind living in, it's Portland, OR. I visited the city for a day during my marathon road trip this past summer, perusing the Japanese Gardens, the Chinese Gardens, and Powel's books. I wish I had had more time to spend there, and had been able to do less driving there; the roads are a pain if you aren't used to them.
The only real thing stopping me is that it's a long way away form my family. Visiting would be Christmas time and the occasional week during the summer. If my family needed me, I would have a difficult time being there for them.
In the end, Portland will remain on my list as potential places to live, but stay at the bottom.