If SSL'ing a site is more than a 10 minute process for you... then I worry about how you go about it.
I think his point was that, if you know what you're doing and you do these sorts of things regularly, yes, it's pretty simple and quick. However, if you're not used to the process because you're not doing it frequently, it becomes more cumbersome and frustrating. For example, on Windows, the process has changed a bit over the years-- not the process of issuing the key, of course, but exactly where do you go in Windows to go through the whole process? What does that process look like? If you want to use the same cert for Exchange, SMTP, IMAP, or other services, where do you go to do that? I couldn't tell you off the top of my head. The whole thing is pretty different from one version to another, so I'd probably have to poke around for 20 minutes just looking for the controls. Similarly, in Linux, I do it infrequently enough to need the instructions in front of me. If you ask me to put an SSL cert on some random shared hosting account, I'll have to go dig through the documentation for that host. My experience has been that the whole process is not hard, but it's not extremely obvious either. You need to be a decent admin who does it regularly to breeze through it.
Now you might ask, what's wrong with that? Shouldn't we expect the people setting up web servers to be decent admins? And that'd be great if we could leave it at that. However, if you've ever dealt with IT professionals, you'll know that the majority of them are not very good at their jobs. Believe me, I've supervised a lot of them, and even the ones who think they're super-brilliant hot-shots are often pretty sub-par. Even the ones that are pretty good usually have their weaknesses, and we all make mistakes.
So honestly, I agree, it should be easier. The process in general reminds me of some pieces of software that I've installed, where after you run the installer, you're supposed to manually run some commands on the CLI, edit some configuration files, edit the registry, or other manual tasks. That feeling of "This isn't hard, but it seems like you haven't thought this all through. You should have streamlined this process a bit."
If you have need of SSL, then you can spend the annual renewal on a decent CA.
I think part of the idea here was that we should all be using SSL. Encrypting web traffic shouldn't be a fringe case of "something used by people with money and expertise". Somehow, we should work on making it the default behavior. It should be cheap (or free) and easy, and setting up a web server without it should provide a bunch of warnings. Hell, visiting a website without it should generate warnings. But if you want to get to that point, then you'll probably need to streamline the process of getting a certificate, as well as making it cheaper.