Portland itself is a nice city. Very interesting place. The climate is a give and take. Summer is awesome. Probably averages about 82 degrees. Spring, Fall and Winter is wet. Lots and lots of rain. It's probably no wonder we took the title of most suicides from Seattle. I personally don't think it's that crowded for a mid sized city. Jobs are hard to come by though.
Cycling is great here and mostly people are quite accepting. Bike lanes just about everywhere.
As long as you can deal with the rain, you'd have no problems with the climate. Basically, you have to ignore that it exists. If it bothers you just a little bit though, you'd probably not make it more than a year or two.
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