Is it so hard for people to learn Markdown? Not just geeks, but anyone? How hard is it compared to learning the myriad of word processing tools that you're expected to know by high school? How much time does it take to learn Markdown compared to the minutes per day that you spend trying to debug the hidden markup of Rich Text/WYSIWYG editors (e.g., why is this text have the same font-weight as the headings now)?
Once the average person learns how to disassociate content from presentation and how markup is the key thing, then static site generators, and the real power of simplicity, become obvious.