Webfaction allows free SSL cert usage, however you have to open a support ticket manually to get a new one installed. Obviously, the 90 day cert lifetime rapidly makes this a pain, especially as you add domains.
I’ve tried to create a tool which automates the creation of new certificates on a schedule, and then emails you (via cron) instructions and some sample text for the support request. The idea is hopefully to make the bimonthly chore of renewing the cert into hopefully less than 5 minutes.
Anyway, if this interests you, give it a shot and let me know how it goes! I’m personally using it for one of my sites and sticking with StartSSL for the rest at the moment. If this makes it simple enough, I’ll end up migrating other sites as well.
Kudos to https://github.com/unixcharles/acme-client for the heavy lifting!