I think you're confusing "simple" with "easy." You may be looking at the controls of a military helicopter for the first time - switches, knobs, buttons, joysticks, etc. and probably feel very confused. But ask any experienced pilot, "Why can't all that be replaced with a single touch-screen interface? Wouldn't that be so much friendlier and intuitive?" they'd look at you like you're out of your mind. For them, those controls are probably the most efficient interface they can imagine.
There's a strong correlation between things that are confusing for the beginners, but over time become incredibly simple to use and things that are easy to start with, but over time they become cluttered, inefficient and frustrating to use. Emacs and Org-mode are not easy to learn, but they can simplify a lot of things later.
I have burned myself with orgmode exactly because of the deceptive simplicity. It did not pick up some important TODO items because of my slight misformatting.
