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?
Do you want to live in a diverse area with a radical political scene, or do you want natural amenities and greenspace and bike infrastructure? Access to these nice things is highly racialized in the US. If you're in the market for $300k homes and a university gig(?), you should consider where you'd be more of a gentrifier than a middle-class neighbor. I can sympathize with seeking better environs and taking advantage of whatever upward mobility you find, but I'm not going to validate a decision to donate $2k/mo to a rando sex pest landlord because the scenery is nice and whites-only.
There is a flip side to having the freedom to migrate that should be considered: intentionally moving to a more neglected area, a place where the marketing and tourism doesn't stick. Where there are kinks to your experience and no real estate developers censoring the unpleasant realities in the local subreddit. Where a white boy airing left views at a city council meeting might punch a little more. It takes more research, but you have to consider the nitty-gritty of what you really want from a place. It sounds like you have the resources to make quite the leap, so broaden your horizons. Wherever you look, be sure to fit in a proper visit before committing to a lease.