This place looks like a good source for free SSL certificates. I believe Jamroom could configure a button in hosting to make it a click for users to set up. It's a non-profit supported by Cisco and other companies. Dreamhost reportedly has a button to install it. Figured I'd run it up the pole here. https://letsencrypt.org .
updated by @blindmime: 08/19/16 11:30:47PM