Nice little town... really more of a suburb of Portland now, what with urban growth and all. Job market is about like everywhere else, not so hot. Can easily work in Portland and live out there, though you may want to live closer to Pdx and drive out to school, especially if you want to be close to town... home prices are dropping and there are tons of places to rent.
Cloudiness... well it is cloudy, but not as much as one would think. Seattle's weather usually gets overlaid onto ours... not a cloud in the sky today... beer is good and plentiful though, as is the coffee, so that compensates.