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?
Yeah..... Colorado prices have gotten pretty ridiculous in the last couple decades. I remember when you could have bought a mansion there for that much if you weren't looking at Denver or Colorado springs.
That's a hard ask anymore in any state that isn't filled to the brim with assholes. Tbh even like places like Minneapolis or Portland the areas surrounding the cities where you can still buy acreage are mostly filled with a bunch of reactionaries that are sometimes more ferocious than in places in the south they don't feel like they're being cornered.
You might try to widen your search to include some more conservative states that have progressive cities in them. For example Madison or Milwaukee are pretty nice if you don't mind the cold.