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 have two friends who had the same idea about the homesteading thing and they moved to Tillamook, which is about an hour from Portland towards the coast. It's politically purple, and you can occasionally find affordable houses a bit outside of downtown on bigger plots like they did. They're not actually homesteaders, though. They both work remote, they just have chickens and some vegetable plots.
You might also be able to find something similar, space-wise, in Oregon's wine country mostly centered around McMinnville. Lots of those homes just seem like bubble-era mcmansions though, I've never looked too hard.