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My wife and I are thinking about getting up out of the swamp. We'd like to find a "kind" state. I started out looking at the Bend area, as we don't want anything west of the Cascades. However, I'm kinda turned off by the resort/golf course culture in Central Oregon. Also, it looks like the only property we'd be able to afford would be in the desert, because we want 5+ acres. Ideally, we'd like to be in a bit of wilderness. So, now, I'm investigating the La Grande/Elkhorn Range area. Anyone familiar with this corner? Is there somewhere better to be looking at in Eastern Oregon? Or, Washington?

You should spend some time in Bend/Sisters. It's evolving. I have friends moving there fairly regularly. That being said, unless there's real industry there, it will always feel like a place dominated by outdoor adventures. If that is your thing, you'll be good. I think Eastern Oregon, even as close to Portland as the Dalles is great. La Grande is beautiful. Eastern Washington starts to feel too barren to me.

I think I'd ask what you plan on doing for $$$. Both of these states have economic engines in the cities and pretty empty rural spaces with out much in terms of opportunities to make $. Another place to look at would be Hood River. Still cheapish land around there, down town has a few proper main street amenities like good food, great beer, and coffee.

Hood river, and east is infinitely sunnier than Portland/cascades. If you aren't too worried about money, I'd also look at Mount Hood area. Zig Zag, Sandy, etc.
If politics matters much to you, Oregon tends to be screaming liberal in the cities, and hard core conservative every where else.

Awesome, that's precisely the kind of response I was hoping for. Thanks for taking the time.

When I first looked at Sisters I thought it was perfect, exactly what we are looking for. However, it started to feel like just a shopping district to serve Black Butte Ranch and the surrounding wealth. Maybe that's the wrong assessment? I did consider the Mount Hood area, too. But, kinda shied away do to its proximity to Portland and Mount St. Helens.

Concerning employment, I'm about to turn 42 and have been at the same job for 16 years. I'd like to work, for someone else, as little as possible. My wife is way into self-sufficiency. She wants to build a cabin and have a small farm. So, we'll do whatever for slight, supplemental incomes.

No problem.

As far as Sisters, it's definitely a Bend satellite. I always liked that it was sleepy, and a little removed. If you could find the right land, it's stunning.

Hmmm. If you can make something work for you that is not dependent upon an established industry or job, you could live anywhere and be fine. I would look long and hard at Hood River, the Dalles and Mt Hood. Mt Hood is not too close to PDX. It's a little over an hour. St Helens is empty. Nothing going on there and the mountain is sleepy.