I'm feeling a bit stifled in my city and want to move. My priorities are $1500-2000/mo rent and a path to an affordable house (see: picture), a unionised city workforce, good greenspace with an extensive parks system, good biking infrastructure, a good public university, and a good political scene. That leaves Portland, Minneapolis, Chicago, and maybe an East Coast city I haven't researched yet. Of those, Portland is at the top of my list because I'm getting an ocean for Great Lakes prices.
What's bad about the city that makes people move away? Is there a better option in Oregon, especially one that would let me commute into Portland without whatever problems it has?
As Femboy_Stalin said, most of these apply to any city in the US, so it sounds like your friend is maybe just jaded about life in the States (fair).
For actual Portland-specific points:
But yeah everything else is true everywhere in the US, I think.
Most of the cool hippies died at a young age, what we have left are the libertarians who like weed