I live in Eugene and will say that the weather in Portland tends to be much hotter in the summers and much colder in the winters. I'm not talking Minnesota cold, just relative to other cities like Eugene.
And, yes, from November to early July it is either cloudy, drizzling, threatening to rain and windy or actually raining. Usually not an all day rain - it comes and goes, but sometimes it can rain non-stop for days. I find no one gets to the point of liking the rain, but you do get used to it - and the fact that you have to just get out there and go about your business, cause if you wait for it to clear up, ain't gonna happen.
I have a friend with SAD, who found herself so depressed during the winters she had to move to New Mexico. and a lot of folks I know do tend to turn to cooking and eating during the rainy cycle.
Personally, I think it would be 100% better than Cleveland, but if you really want sunshine I think Arizona, New Mexico, Las Vegas, California etc. would be more to your liking. Eugene is definately laid-back, mellow and surrounded by nature. Hiking is big, along with bicycle riding and camping. So is Portland, which is the largest city in the state, with lots to see and do. Plenty of quirky little neighborhoods and museums. Price for housing (either to rent or buy is pretty astronomical compard to elsewhere in the state), but salaries tend to be good. Lots of good hospitals in Portland and there are plenty of cultural events going on.
Its a good state to live in, IMHO, but the rain can get to ya after awhile. Would it be possible to take a winter vacation here to get an idea if it is something you could, or would, want to put up with?
In any case, best of luck!