As a lifetime Oregonian, I enjoy Bend and get out there a couple times a year. My family even considered moving there a few years ago in search of a place with more sun. But in deciding between Boulder and Bend, we ended up choosing Boulder, well actually Broomfield, but Boulder was the draw, because as you found Boulder housing prices were too high.
Which leads me to the question, did you consider living outside of Boulder to still get most of the things on your checklist, but not face the high housing prices or difficult political climate?
The problem with Bend, as we came to decide, was there is no "outside of Bend", it's an island with not much of any other place to go for jobs, housing, diversity. Add in the fact that the jobs that are there don't support the house prices. With Boulder, you can always fall back to Denver or one of the many suburbs if your independent business or remote job falls through.
We ultimately moved back to the Portland area for other reasons, but would still choose Boulder/Denver over Bend if we had to do it again.
Which leads me to the question, did you consider living outside of Boulder to still get most of the things on your checklist, but not face the high housing prices or difficult political climate?
The problem with Bend, as we came to decide, was there is no "outside of Bend", it's an island with not much of any other place to go for jobs, housing, diversity. Add in the fact that the jobs that are there don't support the house prices. With Boulder, you can always fall back to Denver or one of the many suburbs if your independent business or remote job falls through.
We ultimately moved back to the Portland area for other reasons, but would still choose Boulder/Denver over Bend if we had to do it again.