Currently AdamShand lives there. I get laughed at when I tell people that it's too big for me but hey, that's just the way it is. Weighing in at about 1.5 million people for the greater metro area it's the smallest big city I've ever visited, with it's emphasis on livibility and neighborhoods it's easy to settle in.
Lots of cheap(ish) and good places to eat:
There's decent snowboarding (though not comparable to AnchorageAlaska) at Mt. Hood and a variety of resorts:
There's even good GIS data available, I guess the city does something useful with the obscene amount of tax they charge you here. You can find crime statistics, property information (prices, history etc), neighborhood boundries, census etc.
They also just happen to have some kick ass CommunityWireless, be sure to check out PersonalTelco. 
Restaurants to Try
Abou Karim - Downtown - Lebanese
Buckman Bistro - SE - Romantic
Noble Rot - NW - Romantic
Salvador Molly's - SW - Cuban - Outdoor
Moon and Sixpence - NW Hollywood - Bar/English - Outdoor