Sorry for the extreme necropost, but wanted to update this thread.
We did a big road trip last summer to scout potential locations. Lovely loop through OR, WA, ID, MT, WY. It's amazing how many great and varied places there are to live in the US. We experienced extreme gratitude during and after the trip because choosing a relocation spot was difficult with so many wonderful options.
Let me start by addressing the title of the thread and assure you that Bend, OR does not suck :) It's a great town, beautiful scenery, lots of potential. The downtown is a little on the small/undeveloped side, but would be adequate for us. I love the high desert and the Cascade Range. Would totally work for us. RE comments about it being "fake" -- yeah, we picked up on that. I would describe it as a resort tourist destination vibe, which then draws transplants wanting to "live the dream" full time. That's all fine, but we realized we don't want to live in a tourist town anymore. Been there, done that. Additionally, it seems to me (from my very limited experience there) that a no-growth mentality has taken root. I totally get that those moving there for the dream want to preserve things as they are, but I've lived this story before and know how it ends, it ain't pretty.
More importantly, we completely fell in love with Boise. Thanks to
@LateStarter1,
@Mele, and
@cheddarpie for the recommendation. The downtown, parks, river/greenbelt, hills, locally owned restaurants and shops, farmer's market, and so much more. Everyone is extremely friendly and helpful. There's a real sense of energy and vibrancy to the city. It feels like a real city, but one that fits comfortably within its footprint, though clear that it's sprawling to the west. We also really like that it has an international airport, and the local ski resort with reasonable prices that's close enough to town. We were even surprised by the extent of the arts scene, not to the level of SF, but more than we expected.
Later on we flew to Boise for a quick winter trip to check things out again and start the house hunting. Easy flight, BOI is a great airport. While there winter conditions were milder than we expected (reference point was living in Germany). I would even say the conditions were nearly ideal for what I like, cool and partially cloudy, with some sun breaking through at times. A couple of months later we ended up buying a house in the North End, planning the move this summer, though this may be interesting with COVID :)
The big surprise for us was Eugene, OR. We put this on our list as a wildcard, but it ended up as a solid second place.
It's been an interesting and busy ~24 months as we explored options and wrapped up commitments here. Thanks everyone for your input, the outside perspective was very helpful for us.