Re: Good boat for learning to sail single-handed in the San Diego area?
The first question is are you going to live on it, or just daysail?. How much cabin space do you really need?
San Diego is mostly light air sailing, which makes singlehanding a bit easier. It's also mostly 'daysailing', as there aren't many places to go 'gunkholing'. For example, Catalina is a very long weekend. For daysailing, you can go smaller, like the Harbor 20/25 in the video; but that's new and expensive. For older/smaller, look at things like a Santana, Jboat, or such. There are a couple of rental places in town that use Catalina Capri 22's - that's a nice daysailer too.
For cruising, you want a bit more space. Catalina 27/30 is not a bad choice, and also Ericson in that range but they are not horribly 'racy'. For what it's worth, I went through the same question lately, and just bought an Islander 28.... except it's in SF, and I'll likely leave it there for a while (the slip fee is about half price).
Craig's list is pretty active here, give that a try.