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?
If you are saying "me" and not "us (at least 3 adults)", this just becomes equivalent to the exurban dream.
Even in the cheapest cities (cutoff being 500k county pop), you are not going to get even 1 acre in easy cycling distance of anything, for a remotely affordable price, unless you have at least 6 people on that acre and build the home yourself. This is a mathematical reality: without extensive urbanist ordinances, radial density of a city will obey a smooth logistic decay function, and land value is proportionate to the output of that function. Suburbs and exurbs have residential subdivisions that stretch to the horizon with the assumption that everyone's just going to commute 30 minutes in a car every time they need something.
However, in those smaller cities I mentioned in the other reply, where the edge of the city's incorporation line often drops off into farmland or woods, you could probably get some okay land for $15k-20k an acre, excluding buildings.