In our area we suffer reverse snowbirding, maybe call it sunbirding... a lot of Cal ppl bought places here for the awesome summertime and a basic skiing fix. Unlike the Denver area, here in N. Idaho the winters are pretty much unridable outdoors from Nov-Apr.
We are not retired yet, but our jobs allow us to work from anywhere with good internet connectivity, so going mobile (hoteling or any of our corp offices) is one thing we are considering for this winter.
50 miles south of San Jose would probably work for us as a ridable area too