Just this week I started learning org-mode by reading one of Charle Cave's postings on how uses org-mode to implement the Getting Things Done methodology http://members.optusnet.com.au/~charles57/GTD/gtd_workflow.h.... For me this has been a great tutorial.
Once I found out how much you can really do with it, I went on a prosetylizing spree and got a couple of friends as well as my little brother into it. Whilst they're somewhat tech inclined, they're by no means emacs geeks, but they got into it after me showcasing and explaining at least some of the features.
Personally, i think that the only thing that's really essential in getting people into it is a tutorial level to it, similar to interactive tutorials for programming languages (I recall a marvelous ruby one from a year or two back, but I'm unable to find it). Org-mode already scales beautifully regarding complexity, and i think the main thing that turns people away from it is that the manual is a literal textbook and only silly people study it back to back. Or that they're using vim and don't want to switch to emacs, but that's not likely the group of people you're targeting.