I moved to the Portland area from California 12 years ago. No one has been mean to me about California, I haven't had trouble making friends, the gray doesn't bother me. I love the weather, it doesn't rain all that much, there's plenty of sunshine *for me.* Apparently not for many others, but I don't really know what they are talking about. The weather here is terrific, in my opinion. A little hotter than I'd like in the summer, but mostly manageable. There's pretty much no rain in the summer. Just day after day of long, sunny days. Western Oregon is so beautiful, I don't really know why anyone would live anywhere else. I'm never leaving.
Summer is gorgeous, fall is gorgeous, spring is gorgeous. Winter is not as nice as the other three, but it's fine. It ends. I've never suffered from SAD so take that into account. Maybe I'd feel differently about our weather if I did. As it is, I really don't know what people are complaining about. If all my neighbors love the sun so much, why don't they go live in Arizona? (I personally ran away from Arizona because it's too fucking hot and the goddamn sun tries to fry your skin the minute you walk out the door. 18 years was 18 too many for me, but you don't get to choose where you're born.)
Portland is a pretty charming city, and a nice size for a city. I spent a lot of years in Los Angeles, so Portland seems kind of small to me but in a good way. I just spent a few days in Seattle and it is lovely, but it struck me how much of a bigger city it is than Portland. Our weather is pretty much the same, but Seattle has a different feeling for sure. And it's a hell of a lot more expensive. (Not that Portland is cheap, but compared to Seattle and L.A., and you're coming from the Bay area? Definitely cheap, in comparison to that.)
I'm white as can be and I haven't tried living a small town in Oregon, so I can't really speak to those things. But based on what you said, I'd bet you'd like Bend. People are always leaving here for a week in Bend so they can get some sun. They do get snow in the winter, though. Sunny snow. :)