(I'm just amazed that LE decided to try modifying webserver config files automatically. There are soooo many ways for that to fail. It's going to take an immense amount of programmer effort for very little gain.)
We're at a stage where people are capable of developing a web application but creating a (suitable) private key, generating a CRL and then using the resulting certificate in Apache is currently beyond their capabilities. Which is kind of cool in one sense but kind of scary in another.
For people who can SSH and install packages, I think they are better served being shown how to add couple lines to make SSL work than some magic that could screw up their web server config. After all, these people chose to learn how to login to the web server instead of just managing their site from a CMS. They would probably like to learn how to configure something like SSL.
You'd be surprised I think.
>They would probably like to learn how to configure something like SSL.
I think you'd be surprised again. It's not even always about aptitude–quite often it's just laziness. The reason that many of these people aren't encrypting today is because they don't want to invest the time and effort. "My copy-pasted openssl commands didn't work? Eff this."
Operations is as much a mindset as it is a skill. Some developers have it, some don't.