* 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.
If anyplace in Oregon were to be Boulder, I'd say Bend has the best shot. Granted, it's an outsider's point of view, but I think it's closer to mountains and at a bit of elevation. Seems like more athletic stuff going on, bigger cycling community and the like. On the downside, it seems as if that main road through town becomes more and more of one giant strip mall. Job-wise, seems like there a few more opportunities than Eugene.
Portland? Plenty going on there, and between Seattle and Portland I'd choose Portland. Seattle wants to be quirky and hip, but doesn't pull it off as well as Portland, IMO. Portland's smaller, too, but seems to have enough going on to satisfy my tastes.
In the end, though, I could find a new job next week in the Seattle area. I lose a job in Eugene or Bend, I'm screwed. That's okay, the Seattle area is nice, too.
Having lived in Eugene for a while, I'd say it's pretty nice, but you might get bored pretty quickly, even as a runner. It's just to small (for me).
I think Portland is better for outdoorsy stuff in general. There's Forest Park, Mt Tabor, etc in the city and lots of camping, hiking, snowboarding nearby.
I'm in San Luis Obispo CA now and, while the 2 cities are pretty similar in size and other aspects, SLO has a much better tech/startup scene.
Apropos of nothing, and deeply OT, don't suppose any HNers could recommend a moving company or three that are good at cross-country moves?