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?
The nice thing about Oregon is you can get "Outdoors" by driving an hour in any direction. Don't worry about the Willamette. There are many many rivers for outdoor stuff that are basically snowmelt clean. If you like the Great Outdoors Oregon might be your jam.
You will want to stay on the wetter Western Cascade side of the state, like Portland, Eugene, etc. Bend, while a great outdoors spot, is the beginning of the eastern Oregon high desert. Great place to visit for outdoors all year round.
The hour's drive to wilderness is the thing I love most about Colorado and why I moved here in the first place. People fly halfway around the world to visit the places that are casual day-hikes to photograph specific flowers or have specific lighting for me. At one point I paid like $800/mo to live next to the trailhead of a hike that gave me panoramic views of the Rockies and Great Plains for breakfast every morning, a really wonderful lifestyle that I want to maintain.