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?
Thank you for saying this, I was going crazy re-reading the original post. It reeks of privilege and escapism, and the replies have mostly been hugboxing.
I've been happy with my decision to move to a smaller place after a lot of critical thought on why I felt a desire to move to Chicago. There ended up being two objectively better options for my needs and life circumstances. It was a headache to try to neutrally weigh smaller cities against the glossy, ready-made big city "experience," but I'm glad I did.
Escapism yes, privilege no, "hugboxing"
OP works in landscaping/conservation and earns well below the national GDP per capita. Being able to take on a 300k mortgage is mid-range for Americans.