I don't live in Bend...yet, but my best friend does and she is recruiting us to move there. I have to say that everything we have seen seems great. Lots of parks, museums, big pool complex, schools seem good,there is a Whole Foods, and a Wild Oats, farmers market twice a week in summer, etc. I actually, although coming from CA, am surprised at how much housing prices have dropped in Bend. A year ago, when my friend first got us looking, housing was considerably higher than it is now. We are excited about the housing market now (except the selling our house part) and my friend said that the people she has talked to (she's in marketing for the town) have indicated that they think housing prices will continue to fall for at least another year, if not more. Houses on the low end of the market are moving, and on the high end, but there are somewhere near 1,000 houses on the market in the 200,000-350,000 price range.
This has been our experience too. We're also from CA and visited friends in Bend a few years back, and loved it. Housing was expensive then though, so we figured we wouldn't really be saving any $$ by relocating. Now though, prices are more reasonable.