Oregon is a wonderful, beautiful place to live. I was born here, and have always returned because it is home. That being said, I am from the Portland area, and the Oregon that is the Willamette Valley is what most people talk about when they say how great and wonderful it is.
I have been to Bend once, so I can't really tell you a lot about it specifically, but I can tell you that it is in the middle of NO WHERE. You are not close to any cities, you do not have access to a lot of specialized care that many families need. The nearest bigish city is Eugene (University town with 30,000) which is about 2.5 hours away, but is not generally accessible in the winter time. Portland is about 4 hours away and is where the majority of amenities are going to be.
Bend is all about winter sports because it has snow so many months of the year. Generally is is affluent people and retirees who live there. The cost of living is high because it is not near a major city. The people tend to be more conservative than those in the Portland or even Eugene areas.
So, how do you like the cold? Are winter outdoor sports important to you? Do you need to see a lot of doctors, specialists, pediatricians? What about activities for kids? Do you need to fly out a lot? There is a small airport in Eugene, but basically you fly to Portland and catch the connecting flights out. Will you be able to find a job?
I hope that helps. If you need more information or help, please let us know!