We were pretty enamored with Bend but decided against it a few years ago for a variety of reasons. From our time there, I get the impression that there are a lot of people who retired or semi-retired with enough money, many from California, who enjoy the combination of outdoor activities, decent food and beer culture, and a dry climate. Totally understandable given the issues that you describe in Santa Cruz, which are probably common in many other places. But, you might also want to consider the likelihood that if you are moving to a place with a lot of retirees, a high quality of life, and expensive housing, then there is going to be a shortage of workers to get things done. Unless you are super self-reliant, you are going to be competing with all those other retirees for people to fix your plumbing, to maintain your roads, to feed you, to take care of you after a knee surgery, etc., etc. Mountain towns all over the west are facing these issues, and it seems like a growing retired population is just going to exacerbate them over time.