I can't really recommend you move to either Portland or Bend.
If the local-trail situation is bad where you are, I can guarantee you it's worse in Portland. There is very little mountain biking that can be considered "local" (though i seem to be one of the few who actually enjoys Forest Park in the winter, and I mind don't the fact that the Sandy Ridge climb happens to be on pavement). There's a great diversity of trails within a couple hours of here, but you always have to drive a ways to get them. If that's also true where you are in ID (I realize the stuff I mentioned above may not be local to you), the situation won't be any better in Portland, though the job market may be. Of course the market's still tight here, but at least it's a big city with a wide range of employers.
And Portland can indeed be gloomy for half the year. It's been especially drearythe last 3 years (this year's spectacular summer notwithstanding!), and even many of us who normally don't mind it -- including my NW native wife -- are getting a little grumpy. At my home's rain gauge we saw 8 inches of rain in October, 10 in November and 6 so far this month. Put in perspective though, that's well over half a normal year's allotment, so maybe we can hope for some drier years coming to even things out.
As for Bend, the riding and the climate are great, but the job market really can be difficult and the pay low, except for a few industries. If employment was better in Bend, half of Portland would move there in an instant. Low pay is the market's way of reconciling Bend's limited job market with the almost unlimited demand of people who wish they could live there.
Actually, for a few years we had our eye on Boise as a potential place to move to. It has a nice dry climate with some semblance of a "real winter" that's missing here west of the Cascades, a lively and fun urban core, tons of nearby recreational opportunities that don't require long drives, uncrowded mountains ... and a much bigger job base than most towns with those attributes. I think we've realized we're pretty dug-in in Portland and will be staying, but my wife and I have for quite a while referred to Boise as "Bend, with jobs." Not a ton of jobs -- things are still tough all over -- but certainly more than Bend. If I were you I'd hang on in south Idaho a while longer before giving up on it.
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