I know that Emacs and LaTeX both have newcomer-friendly tutorials, that's how I learned them initially. In Vim, I only know about 5 commands, that's enough to get simple edits done when emacs is not installed. So I don't rate any of these as poor for new users, as long as the new users can find the tutorial.

Let me give you an example of a complicated product where the user-interface can be made friendlier. I worked on a C/C++/Fortran compiler (PathScale) for a while. Users would compile non-standard-conforming programs, get the wrong answer, and then tell us that we had a bug in our compiler. I got the compiler guys to add some compilation flags for things like "use C argument aliasing rules in Fortran". Then when a user reported this class of bug, we had a section of the manual which said: "Compile with these flags. If you now see the correct answer, figure out which flag fixed your program, and then go read the appropriate paragraph in the manual explaining how your program is not standard-conforming." It worked great for both our in-house customer support people (who used it all the time) and customers (who might use it once or twice, usually after being prompted by our customer service people.)