* Eugene is a smallish city with a the University of Oregon. If it played its cards right, it could be something like Boulder. But it doesn't seem like a lot is going on there, and the weather... well, it's pretty grim, like all of western Oregon. In my opinion, 5C and rain is worse than some snow from time to time in terms of 'bad weather'.
* Bend is kind of on the small side to have much going on, but maybe has more than Eugene for its size?
* Southern Oregon - Ashland in particular, is a nice place to live as it's a bit drier than further north, but it's still on the smallish side, and I don't know that there's really much of an 'ecosystem' there. I could see living there if I had a bootstrapped thing going and wanted somewhere cheaper to live that's still nice in some ways.
* Portland is big enough to have a real community, and is a good city for the right kind of person. I can't stand the weather myself.