Portland might not be the most Democratic city but it's arguably the most leftist city (yes, even on economics). It's not upscale outside of a few hilly neighborhoods on the westside and has a disproportional large lower middle class alt community that I'd argue is lacking in SF and Seattle. If we had a significant left-wing third party candidate ala Nader in 2000, Portland would probably give him/her the largest percentage of the vote at this point. Portland keeps attracting more and more young adults without gentrifying rapidly.
Portland's numbers never live up to the hype. But I'm listening. Show me some data. Present some facts.
The problem is that it's difficult to find precinct results for many elections in Multnomah County. I've found 2010 Gubernatorial results and all of 2008's results but nothing else. I suppose I could check the library here for an electoral history of Portland and post maps/data? Which initiatives and referendums do you think would be good metrics for leftism?