I'm going to throw in my two cents- I promise I'll leave it at that. I
have done just that on other issues.

I've only been using TW intensively for a couple of years, and as I've
said elsewhere I "bounced off" of it a few times- repeatedly became
interested because people I respected were enthusiastic about it,
tried to learn about it by reading web sites, downloaded it, played
with it a little, failed to "get" it, and drifted off-  and I'm a
nearly ideal case, I've been a professional programmer for a very long
time, and was an amateur before that- this stuff is more than a living
to me, it's something I'm passionate about. It still took me perhaps
four distinct attempts over something more than a year before I
started seeing the possibilities, and how it would be useful to me
personally. Most people encountering it for the first time are
probably not hard-core technophiles, and aren't likely to devote that
much time.

I think the person investigating it "cold" wants to know those two
things, and probably within the first 5 to 15 minutes; What is it, and
what can it do for me?  Unfortunately, IMHO, those basic first
questions are the weakest point of practically all of the information
sources that a beginner will find. Much of what is available has
clearly been written by people who have been "close" to it for a long
time and have forgotten what it was like NOT to understand the basic
concepts yet. A lot of sources don't even try, they presume some
familiarity instead.

I am NOT saying it's a trivial task. I'm not at all happy with my own
attempts (on my  web site), so I'm certainly not in a position to give
specific advice to anyone.  IMHO, the "single-page application"
paradigm is just that- a new, different concept for most people.  It's
a great deal like trying to explain the first computer spreadsheet to
someone who's never seen one or even heard of one- mostly we're
reduced to giving specific examples which may or may not be relevant
for the reader, or just saying "just try it", which is pretty much
just giving up in frustration.

As I wrote on my site, one co-worker I introduced to TW said something
I find very interesting- she said "it's like your own personal web".
Clearly that's not accurate in any technical sense, but I think it's a
valuable insight as to how someone coming at it "cold" might first
begin to perceive it's value.

All of the issues about how information should be stored and presented
to those already interested in modifying TW for their own purposes is
valuable and clearly worthwhile, but those are also much more
tractable tasks for technical people.  A more difficult task, but to
my mind more important in the long run, is answering the most basic of
questions for a not-terribly-technical audience- what is it, how is it
useful?  If we can't answer that for people of different backgrounds
in a paragraph or two, and I don't think we have yet, we'll always
severely limit the audience for anything that comes after.

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