registerfly.com - I picked up a SSL certificate for www.cwinters.com so I can read my email securely. (Never know who’s spying at work…) I went with RegisterFly (weird name) because of the price ($10/year) and the fairly straightforward registration. I filled out my information, verified my email and then activated a phone callback system that called me and asked me to enter a verification number displayed on the screen. (A decent amount of cluefulness: I actually activated the phone callback system a few hours later from home, but recognizing the potential temporal difference they’d given me a URL to make it happen very painlessly.) I probably wouldn’t propose it for an e-commerce site – they have a higher priced cert with insurance for that – but for my purposes it was perfect.
FWIW, I did think about using CAcert but that forces the browser to accept a new certificate authority (or whatever). If it was just me I wouldn't care, but nongeek family members use webmail on this server and I don't want to have to explain it again and again; $10/year is a small price for laziness.