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You've asked the equivalent of the 'do-everything cartridge' question. Too open ended. It depends on what you like. Answers all over the map and you'll adhere to them based on the biases you had before you asked the question. Here's an example of a useless answer:

If it were me, cut out the Willamette Valley and the coast (too wet for my taste, and you most of the people too). Cut out the Columbia Basin (nice to visit, but don't want to live there). That leaves 70% of Oregon remaining. And it's a nice 70%. Good towns with people who you would enjoy for more than a visit. Beautiful land (pick you favorite from desert to scrub to canyons to mountains). Drier climate, and a full four distinct seasons. And plenty of the non-human spaces in between.

There are far more good places to go get lost than popular culture would lead you to believe. It's your twilight years. Go be in a place that makes you envious you didn't come there sooner.
nice "what-if".... but that is not what is happening. I guess hope for the subduction.
 
Realize that one of the reasons for leaving someplace is that too many people are moving in. So, you're going to go somewhere and "move in". As human population grows, places get filled in.
 
Let's say you came out to Oregon 25-30 years ago, fleeing a socialist paradise back east. Now look; yeah, PDX is not so hip any more. What if the time were ripe to get outa dodge, and as my old mentor Uncle Remus advises, "stay out of crowds at all costs"?

If you were going to retire, and try to grab a little piece of land with a view, far, far away from Utopia (as it's defined today by our progressive betters), with less than $200k, where would you go? Assume you desire to stay in Oregon except for Multnomah county and the surroundings. Josephine County? Up the gorge? Coast?

Where would you NOT go, at any cost?
interested in this thread as well. Came to Oregon in 2003 - job relo. Had been in bay area of CA for 3 years prior with the same company. We are originally from the southeast (Carolinas). about five years away from retirement. No plans to stay in Oregon (just too blue, and the climate) - sorry. And we won't be forced onto a hard winter reservation - i.e., no midwest, north central, no further north than Oregon. Read recent article in some news rag about people migrating out of blue states to escape the messes they voted for and going to red states like Texas, Florida, turning them 'purple'. Sheesh. Not looking to isolate on a piece of land and go off grid. Need access to health care and amenities. So yeah... looking for options.
 
As we age, healthcare access will be critical. Even before Covid many of the rural areas were losing doctors and hospitals and healthcare support. Depending on your particular situation, locating reasonably close to a area with the necessary facilities will be necessary.
 

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