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 white supremacist history of Oregon definitely gives me pause, but Colorado is already so deeply reactionary and troubled that it might somehow be an upgrade.
Milwaukee is also definitely a consideration. I like the affordability of it but have only ever been to the Greyhound station so I don't know their infrastructure.
I was very impressed with the public transit and biking infrastructure in Milwaukee FWIW
I should add the other thing I like about Milwaukee is that it’s only like 30 min from Chicago so you can get Milwaukee prices while still being able to go do stuff in Chicago.
Really closer to an hour, in absolute best conditions, but often 2 hours or more with traffic and parking. And a 2-hour drive includes 90% of the country.