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?
I bet if you asked people who are leaving, they'd say they "feel stifled in their city". And people say this everywhere. That's the problem with shopping around like it's a menu: you're consuming the city as a novelty, and nothing ever remains good enough.
The factors that really matter are the connections you make, the quality of life you get, and the things you absolutely can't live without.
What level of public university is "good"? Does the city have to be big enough to have an international airport and pro sports teams?
I don't live in an urban area that spans multiple counties (or multiple hundreds of square miles, for comparisons west of the Great Plains). I have a job with a rather modest wage but I save about $1000 a month. Property taxes here are often below $5000 a year. There's a college in town, a mostly complete retail diversification, and cultural stuff from all over the world, but I can still easily ride my bike over to the wilder spaces. On mass transit I can get to multiple big cities for less than $70 if I so please. And I feel more relevant and connected and even powerful here than I ever did in the big cities I've lived in. I suspect there are dozens upon dozens of places like mine. There are at least 3 that I could basically move to whenever I wanted.
If you dream about Portland and your heart is set on Portland then move to Portland. (Or Eugene or Corvallis, or maybe Salem, idk.) But if you just crave "something new", search deeper for reasons why.
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.