It's got a lot to say for it, and it's not too cold, but that gray weather can be a real downer. Source: grew up in Eugene. I would visit in November or March and see how it goes.
Ashland has dramatically beautiful surroundings and an active arts scene, but it's a long drive from major urban areas and the "university" is a very, very minor outpost of higher education.
It's not super clear what OP wants, but Ashland offers a ton more than just a 'small town with a few stores'. The problem is the cost of housing, and that some years that whole valley fills up with smoke.
