I've given a serious look at moving from Seattle/Redmond to somewhere in Oregon outside of Portland. I'd love to live in Eugene. As a runner, that place seems like Disneyland. But as you say, the town doesn't seem to have made much effort to be even a very good college town, let alone have much else going on. I could still live there, but tech jobs are a bit slim.

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.