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?
Portland's nice but a few things: It's on the Willamette river, 2 hours from the coast. And the coast of Oregon is pretty mountainy and stormy. It rains a lot in Portland, so seasonal depression can hit everyone for like half the year. If you don't already have a job, there isn't much industry in Portland proper aside from healthcare, government and higher ed. The neighboring cities have some options like Intel and Nike. Oh also the state has a super racist history, used to be a whites-only state that confederates moved to after they lost the civil war. Portland proper and some of the neighboring areas there's a bit of diversity but outside that its pretty white and racist.
Outside of these things, it meets your other criteria
The gloomy climate is a selling point if anything. My bones yearn for what used to be English weather and Colorado's high desert water scarcity makes me too anxious. Is the Willamette river and that general surrounding watershed nice for recreation or is it too polluted like a lot of midwestern rivers?
Willamette is safe to swim in except for during very heavy rains when the mixed sewer system gets full and sewage will go into the river (only happens once or twice a year, and only during the winter, when you probably don't want to be swimming anyway) and during algal blooms when it's very warm out (a capitalist created basically an algae breeding ground and has been ordered by the state to fix it, but is slow walking it obviously).
There's a public swimming dock on the river. It gets really popular on the days over 90. This past summer there were organized group bike rides every Wednesday to go swim at the river.