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Portland is a funny place. It is not a small town but when I was there it was unusually quiet and laid back, but not in a depressed way -- it's all working as intended. I associate streets like these with bigger crowds than what you see in these photos. Portland reminds me more of, say, a larger version of Victoria rather than a smaller Seattle or San Francisco. It's not a small town or a rural area but it's not a place you move to if you want big city life.
It is attractive and more affordable than most other West Coast cities. It's easy to see why a lot of people like it so much.