It really depends what you are looking for. Close in westside homes are the easiest to walk to shops and downtown, but are often older and smaller. Northwest Crossing is on the edge of the westside and is near the bike trails, although not really walkable to town and the commerce in the neighborhood is not going as well as planned. The houses are all newer, bigger, and mostly built with care. Certain neighborhoods were completely built out by specific builders that aren't known for their quality. I've seen some cheaply built ones east of NE 27th st that don't look like they will last 20 years. Next place to check if you can afford it is Awbrey Butte.
Be aware that we are starting to see massive foreclosures, and the less established neighborhoods will be hit the hardest. Estimates are that 60% of owners who bought in 2006 are underwater and almost 50% of 2007 buyers. Neighborhoods that were mostly built after 2004 or 2005 are going to have a lot of distress in the year to come. One subdivision (Newport Gardens) near NW 14th and Newport has had 7 of 14 lots go into default by the people who own the houses - not a developer going under. Of the 14 lots, not all have houses on them. 5 of 6 of the houses that are built on Newport are in default or already bank owned.
In four of the last five months we have had more Notices of Default than sales in Deschutes County, and in December it was more than double. January's defaults are looking to be much higher than December's. With this in mind we will probably see greater price declines in Bend than we saw in 2008, which ended with medians down to $224.5k, down over 30% year over year. I am predicting sub $200k medians by March. We should see sub $170k by late fall, and $150k by spring 2010. Where it goes from there is going to depend on inflation.