See the dilemma?
For example, I'm on an Ubuntu machine now, and I've recently tried to upgrade it, but apparently it's too far out of date. I've tried to install some software, but it can't find the necessary site that has the package. So now what? I have nowhere to go apart from the internet, and suddenly I am once again having to learn stuff that I really don't want to have to know.
Again, this isn't a complaint, it's an attempt to help define and clarify the problems faced in getting Ubuntu (and other distros) more widely adopted, something I would love to see.