I lived in Bend from '07 to '10. It's a great city and I miss it but I don't think it has any shot at being the next Boulder. The weather is better than Eugene but there's no university, its a fairly isolated city, and there's not much of a local startup/tech scene. I could never find a local developer to hire.

I'm in San Luis Obispo CA now and, while the 2 cities are pretty similar in size and other aspects, SLO has a much better tech/startup scene.