Unfortunately, my only experience cycling specifically in San Diego is racing. I'm actually about 4 hours North of it. The weather is still pretty nice here (if you want info on Los Angeles County, let me know), but it tends to be more consistent down there. If you are indeed enticed by this possibility, I suggest coming over to the So Cal region and posting there. I know quite a few members who would love to post routes, suggest hotels, and probably even ride with you.