Right this is exactly what the Letsencrypt folks are trying to solve. Thank you for your work Josh! SSL has been a pain in the ass for decades! Generating certs, deploying them, maintaining them. This is why we are not at 100% SSL on the web. The LE folks are trying to fix this. Please send a few dollars their way on their fund raising page to help this goal along.

It's not unobtainable to make using certs MUCH easier and automated, their work should be supported by us all.