I live in Portland. It's obnoxious in many ways, but I like it well enough. Although the economy isn't great and we don't have many large employers, rental prices aren't especially high and people don't really have to scramble to make ends meet. Thousands of slackers manage to live quite comfortably here.
The hipsters and SWPLs are indeed obnoxious, and there's definitely an ideological mold that everybody feels pressured to conform to in polite company here. That said, they do create demand for a number of amenities that I appreciate, most notably pertaining to food. There are a ton of good restaurants, brew pubs, dive bars, diners, overpriced gourmet grocery stores, Trader Joes (which I love because it sells good food that's cheap), farmers markets, etc.
Also, I'm a cyclist who transports myself everywhere by bicycle, and and it is quite easy to get around by bike here. However, other cyclists in this town annoy me, as at least half of them do not obey traffic laws, which both puts me in danger and and gives the rest of us a bad name. I don't like the evangelical fervor with which cycling is promoted here -- it's treated too much as a religion, rather than as merely a form of transportation and recreation. Oh, drivers and pedestrians here also suck ass -- the drivers are distracted and have absolutely no sense of urgency in getting from point A to B, while the pedestrians lack any semblance of common sense and think absolutely nothing of stepping into a street without looking both ways.
The scenery that surrounds Portland is amazing, even if I rarely find myself exploring it. You have mountains on both sides of you (with snow to the east) and lots of forest. The Cascades have plenty of winter sports opportunities, and the whole state is good for mountain biking, hiking, etc. during the summer. In Portland itself, you'll find yourself staying inside for most of the year because it's wet and miserable. The summers are glorious but brief.