It seems to me that many people who are Windows-entrenched, even if Microsoft causes them grief, will stick with it because they don't want to learn a new OS. Me, I never really did learn any OS, so I was a good candidate for starting on Linux.
I even learned how to write shell scripts and picked up regular expressions, but had no idea these had anything to do with "programming" until I went to a LUGOD talk on regular expressions. To me, they were just "commands". I learned how to use them in answer to, "Mike, how do I get my computer to do [this-or-that]?" He'd say, "oh, yes, that's very simple: here are the commands you need, watch where you put spaces, here's what the pipe is for...." Sometimes I'd get unexpected results (like if I typed a capital L when I should've used a lower-case one), but it's no worse for a user than choosing the wrong option from a bazillion choices in pull-down menus.
A while back, Mark and Bill were teaching a week-long intense Linux class. As I recall, people would come out of those courses knowing more about their computer than many Windows users know about their computer after years of using it. Penguin Power!