Hi James.

If you do not grok text its unlikely you will appreciate a text editor.
emacs is not just a text editor its an exceptionally powerful text editor -- a power which is likely to alienate you even more.
So the best suggestion to someone who wishes to get into orgmode but finds text (and text editors) unpleasant is to give up on orgmode, just dig into emacs' simpler uses for a while and when a little more comfortable (with emacs) try org again. Hopefully then your questions will be more focused to this list and the answers will be more useful to you.

That said, there is some merit in (some of) what you say.
org is so many different things at the same time that for a noob to find one's way through the documentation to make his usecase work with minimum pain seems to be unnecessarily hard.


The beginner's customization guide:
http://orgmode.org/worg/org-configs/org-customization-guide.html
is of course a starting point.

But I wonder if it would be possible to structure it into something like this outline so that different beginners could start at different places?

* Brainstorming-n-outlining
  TAB and the basic structure navigation and editing features
* Exporting and Publishing
*** html export
*** Odt export
*** Web publishing
*** Latex publishing
*** Presentations
***** Lightweight options
  http://orgmode.org/worg/org-configs/org-customization-guide.html
***** Beamer
* Babel
*** For programming
*** For teaching programming
*** For doing science (R)
*** For scientific publishing (R+Latex)
* Time/project mgmt (GTD)
*** Agenda
*** Time tracking
*** capture-archive
*** Journalling
*** org-habit
* Tables and spreadsheets
* Integration with other emacs uses
*** gnus
*** bbdb/ org-contacts
*** firefox (org-protocol)
*** graphics (R, ditaa...)