I grew up there, and while I haven't lived there for some time:

* 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.

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.

It seems to me that one of Boulder's big advantages/draws is that it's a college town close to a big city (Denver). There's no arrangement quite like that in Oregon. Bend is hours away from Eugene or Portland.

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 not entirely sure if it's size related or... just lack of energy/ambition. Padova, where I live now, is a similar order of magnitude (214,000 vs 150,000 in Eugene), but there seems to be more going on here.

Yeah, that all sounds about right. The reason I don't see Bend as a future Boulder is that it doesn't have much in the way of higher education. The big universities in Oregon are in Eugene, Corvallis, with some other stuff here and there. Corvallis might not actually be bad in some ways, although it's pretty small. Might not be a bad place to bootstrap a company.

Shh! don't tell anyone how awesome Portland and Bend are ;-) Lots of good things happening in both places. You are right, in Seattle you can have a new gig an hour from now if you want it, but it is expensive and pretentious. I grew up there, love it, but left three years ago...sure it isn't SV, but still too expensive and terrible commutes.

I lived in Bend from '07 to '10. It's a great city and I miss it but I don't think it has any shot at being the next Boulder. The weather is better than Eugene but there's no university, its a fairly isolated city, and there's not much of a local startup/tech scene. I could never find a local developer to hire.

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.

As a data point, I recently switched jobs to a 100%-remote-working arrangement with a company based in Oregon (Portland). My plans for the next year involve a move from Boston to Flint, MI (family-related reasons), then a direct bounce to the Oregon/Washington area 'just to check it out'. Depending if the job holds, I'll probably stick around there for the change-of-scenery aspect for a few years, then perhaps start considering moving internationally. If it matters, I'm smack dab at the beginning of the article's "30-45" age cohort, no kids, no plans for kids, no desire for kids. I do have a dog and a penchant for playing music with other people though, so that's kind of the same thing, right?

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?

Check out http://upack.com and http://moveline.com

No direct experience with Oregon, but a casual search on indeed.com revealed a bunch of Insurance/Healthcare related tech work. It looks like it has a healthy sector there, but the volumes of open jobs don't seem to compare well to Seattle and definitely not SF. Could be wrong though... this is a very qualitative observation.

I don't live there, but I live in the general area and try to follow the tech scene there. I think your observations are partially right - there are the usual suspects: Nike, Mentor Graphics, Columbia Sportswear, Intel, etc... BUT, there is a vibrant open source and small software company scene that is partially under the radar - they don't post on the "name brand" job search sites, but if you get hooked into the local tech network, there are lots of great opportunities.

I think it is growing slowly, partly as a spinoff from SF. If you want a lifestyle, it is a great place, but if you want a career I would suggest paying the rents and going to Seattle/ SF/ wherever.