I shall chime in a I have lived in or close by several of the OR & WA communities mentioned.
Eugene (my natal & university town). Great combination of affordability and activities. Liberal orientation. They have an airport but most drive to Portland (I-5 is getting beastly) in about 2.5 hours. The nearby ski area is so-so (wet side of the Cascades), easy drive to the coast all seasons. Because of the U of OR there are lots of activities and performing arts opportunities.
Ashland is a quaint university town with a strong performing arts (theater) culture. Situated in the foothills of the Siskiyou Mountains it has a real winter. Small ski area just south of town. Not far from Crater Lake and Lake Shasta. Don't try driving to the coast in the winter, more than one vehicle has come to an unfortunate end.
Bend has gotten expensive. It is cold in the winter and hot in the summer. Great skiing, great for hiking and camping in the Cascades. Not for folks at risk for skin cancer. All the communities east of the Cascades are sunny, the Cascades wring the moisture out of the storms (you didn't read that, right?). However, they are on a high plateau and are downright chilly in the winter. The Redmond Airport serves Bend and is busy (beats driving over the mtns in the winter!).
Portland is even more expensive if you want to live in the city center - almost NYC prices IMHO. The further from the city center the more reasonable the housing cost. I am oriented to the west side so were I a single woman I would look around Orenco Station. Getting into the city center or the airport on the Max is a slam dunk. The 'hip part of Portland right now is the "Pearl". We old timers who remember the warehouses and sleazy bars of yesteryear roll our eyes, but it has gotten to be a fun neighborhood. Not far from Powell's bookstore. What amounts to a pub-crawl the first Thursday of every month. Portland has several senior non-profit residential communities, should that ever interest you.
Sequim, WA has a mild climate for this latitude. Getting to SEA airport is not easy. Urban oriented folks would need to make a huge adjustment.