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 plows and winter road care are very robust, at least in my area. I'm in Central Minnesota, north of the cities. If you live on something like a homestead (we're on 3 acres off of a county road in mostly farmland but still paved) you will want a 4wd vehicle maybe 1-2 days a year based on my experience. Otherwise I can't imagine it'd be any worse than MI, but I also work from home and my "commute" is taking the kids to school in the morning. So... It can be sketchy, but usually not long.
If you wanna watch it play out in real time keep an eye on 511mn.org over the next few days. We're supposed to go from pretty warm (40+ F) to 5-10" of snow pretty quickly. This will let you directly see how things get plowed and even the highways and roads themselves look via the camera systems.