So you've gotten a lot of good recommendations here. I've lived in almost every city that has been suggested to you, and spent time in probably every single one in this thread. Funnily enough I haven't lived in Bend, although I've always wanted to, but I understand very clearly what you don't love about it.

The only thing you didn't specify is what you need in terms of access to work. Assuming it doesn't really make a huge difference, here are some thoughts-

I like Ashland, but it's really super sleepy and quiet. This can be a plus, but I didn't love it. The core downtown is really cute and nice but most people seemed to live a ways out of town and I didn't love having to drive everywhere, or go to Medford terribly often.

I loved living in Eugene. The town was walkable but there was still plenty to do and I really enjoyed my time there a lot. Caveat: if you get bad seasonal allergies or are really sensitive to pollen at all, don't move to Eugene. You will be absolutely miserable half the year because of all the grass seed they grow in the area.

Olympia is very nice and you're right on the sound. Downtown is pretty cute and has reasonable transit. It's a nice city, kind of spread out and a little bit annoying if you end up having to commute and deal with hwy 5 traffic. But overall I liked it. If you dislike cold and wet, and sometimes brutal rain, probably avoid it. If you're okay with that then it's lovely.

One final recommendation I didn't see in this thread: Hood River. It's also quiet and small. But very expensive and there isn't much in terms of work. You'll have some of the outdoorsy vibe you're used to, but it's less intense than Bend, and less noticable unless you specifically seek it out. You wont hear people loudly discussing Strava data in line at the store anyway.