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 used to live in the PNW and now live near the Arctic Circle in Scandanavia. I would absolutely kill for Portland sunshine.
SAD can be an issue but I always go somewhere sunny for at least one week in January (the heart of winter) to get some vitamin D. If OP has a good job going south in winter (especially to the desert) is a good option. Supplements can help with SAD as well.