Hey there! Long time Oregon resident here, I'm currently in Boston for a while longer, but I am returning in August!
One thing I will tell you about Oregon, is that it has everything! Kayaking, snowboarding, deserts, ocean, sand dunes, volcanoes... but none of it is particularly close to each other!
is a pretty solid balance of everything, and one of my favorite cities. If I could find a good job there I'd surely relocate there, although now that I'm working remote I may just buy a house there! Good snowboarding nearby, long(er) dry season then west of the mountains, a pretty good culture going on, and in general a pretty nice and outdoors oriented attitude. It's a great city. Amazing food options are to be found as well! VERY COLD WINTERS!!!!!!
People there are generally younger, but it's still got a healthy balance around it. Lack of major industry or tech tends to have successful people in their 30's heading elsewhere.
What it doesn't have in the immediate vicinity though, is just a few hour drive away though. That's a common story for anything in Oregon.
is a rad city, but it's become a bit of a dog pile. LOTS of highly educated people competing for jobs driving the pay scale for jobs way down compared to other cities, with a serious shortage of housing driving home prices (and thus rent) way up.
Portland is short drive to Mt. Hood (1.5 hours away, like all good things in Oregon), which has plenty of good snowboarding and seriously giant amounts of snowfall, plus a longer season than Bachelor. Terrain is milder but still plenty of challenge to be found. Lots of good rivers nearby, ocean nearby, tons of great food and culture, great spot. Plenty of white water stuff to be found within a reasonable drive.
Way more people in our age group (early 30s) living it up in PDX. Half of them are Baristas chasing the dream of their band making it big someday still... but there's still a big contingent of outdoorsy rad people to be had
Eugene Oregon is a very cool and progressive city. Lots of cool things going on down there, decent rivers nearby (again, 1.5 hours drive) and all sorts of stuff to do. Good food a plenty, fun little spots... LOTS of teaching to be had there. NOT a lot of culture... but hardly backwoods either.
Ashland seems to be a rad place. Better weather, decent stuff around, Mt. Ashland isn't miserable, but it isn't amazing either.