Re: Single-handed Sailing, So. Calif.
I singlehand my Cal 2-30 at least twice a week out of MDR, like Mike, mostly mid-week. It's comfortable going coastal or over to Catalina. It's the only boat I've ever had, so I couldn't compare. Mine is cockpit rigged and has roller furling, fin keel, tiller steering on a spade rudder. I don't use an autopilot. I only leave the cockpit to grab a snack. The waters here are pretty reliably tame. I see no reason to go smaller (you could always rent a dinghy sailboat if you wanted the sport of it). If I feel like tacking out of the channel, I do. It's good practice and when traffic is light, no one cares.
1968 Cal 2-30