How are you liking Bend? I remember reading some of your comments on HN a few years ago since we were living in Portland. In Seattle now and own a place, but are thinking someday we might sell it and move to Bend. We've always found central Oregon uniquely beautiful. My friend just bought a place in Boulder, and I visited and enjoyed hanging out there. Things did seem a bit more expensive.
Up: Bend is a rad place. The lazy river / float scene is really fun. There are approx. 26 breweries, great food, and a really active community. On a typical weekend everyone is out and about which makes it easier to meet folks and get integrated into the community.
Down: Bend was not built for the massive influx of people that the city has seen in recent years. The transportation group is trying to work through it but they will need to be very creative as there is a nice distance gap between East Bend and West Bend.
There are also lots of traffic circles that are single lane that seem to slow down traffic (good and bad) but they run right up against homes and businesses so there are not many options for expansion.
If you own in Seattle now is a great time to sell. We moved a year ago (enjoyed Seattle and its quirks/beer/outdoors) to a more Bend-like community and run our business from here. The transition was worth its weight in gold and we don't look back one bit.
Why is everybody mentioning Bend? Is there a big tech scene there? I used to live in Colorado so I know there's a lot of tech companies in the Boulder area, but I've only been living the the PNW for a few years and haven't heard much about the technology scene here other than everything up in the Seattle area (Microsoft, Amazon, Boeing, Valve, etc.)
Summer in Oregon is wonderful, no two ways about it. What we'll have to see is how the winter is over here. I grew up in Eugene and lived in Portland, and just can't handle that endless gray.
Hopefully we get back to the "normal" Summer in Oregon relatively soon (not looking likely thanks to the Blob/El Nino). Living in Portland without an AC this Summer has been terrible.