Blazer's Edge's own Evans Clinchy recently published a piece on Portland fandom at The Classical. In it he describes the endearing and quirky outlook of Portland Trail Blazers fans as they remember past glory and cope with present pain. He also gets in a few lines about living in the city itself.
I moved here last year. One close friend, when I told him of my plans, laughed and mockingly told me that Portland was "where young people go to retire." He wasn't wrong. Portland is a wonderful place where nature surrounds you, the vibe is pleasant and craft beer flows like water, but you can't shake the feeling that you're in a wasteland of hipsterism where having a career takes a backseat to trying out that new food truck that's down the block from that other food truck that's in the vacant lot around the corner from that thrift store. The city is laid-back—lovably so—but you occasionally get the sense it might be too laid-back for its own good.
As far as Trail Blazers fandom...
The fans here are undyingly loyal. It's buoyed them through all the microfractures and torn tendons. In all likelihood that loyalty won't be rewarded this spring—we're probably just days away from witnessing the Blazers' graceful exit from the playoffs as stronger, healthier teams survive and vie for the Larry.
Different cities might process that pain in different ways. Minneapolis has been bemoaning its terrible coaches and executives for decades, playing the "woe is me" card so many times it's become wrinkled and faded. Cleveland has immortalized all its failures in overdramatic fashion, giving them two-word sobriquets where the first word is "The" and the second is "Drive," "Shot," "Fumble" or "Decision." Portland's a little different. The prevailing feeling remains one of optimism—a feeling that, if this town sticks to its convictions and supports this team for long enough, eventually good things will happen. In short, they're still just chasing that next sunny day.
That's just a sampling of the article. It's well worth a read.