These  are all my opinions, of course.
 

The lack of proper end user documentation is one of the main problems
with ConTeXt.
Eventually, actually one of the main problems is the lack of
people like Wolfgang  Schuster .
For sure the things can be better if everyone uses  the wiki to search and update documentations
or write solutions.

There was talk of a book about ConTeXt but I haven't
heard about that one for a while. Probably impossible given the lack
of stability (aka ongoing development) of ConTeXt.
mkii is not so instable.
mkiv is under active development,
but I'm using it for a catalog from  october of last year.

ConTeXt could become very popular in teh TeX world if it had:
- A decent versioning support (where you can get documentation and
code that match and not code from 2008 with documentation from 2001)
- Side-by-side development of manuals and code
More or less, TeX and Latext suffer of the same problem.


As it is  now, the developing community is restricted to the few gurus
who can hack the ConTeXt source code.
From what I know,
the developer of ConTeXt  is Hans Hagen.
There are some texnicians
who help in debuggings; there are some people (wolfgang,mojca, aditja,...)
who know context better than others and offers their support
on the mailing list (we also need more people like them) .
BTW, we are lucky
that developing is firmly on the hands of Hans.



No other sane person will try to
release and support something on such a volatile foundation.
It's no true.


What
ConTeXt looks to me currently, is a personal swiss army knife of a few
people who have no need for end user documentation (so it never
arrives).
ConTeXt/mkiv actually is the most advanced macro_packages_system build on top of luatex,
the successor of pdftex; it's a serious competitor in the world of typesetting systems.
With lua build in, will attract more 'traditional' programmers than tex/latex/pdftex etc.
It's an ongoing process of development, because it's not easy to develop luatex-mplib-mkiv
in synch (and taco is another giant )
It can be true that actually context is hard to learn, but I don't think that this is the right moment for a book.


And to be clear: without luatex, TeX will not survive.

Only my 1cent.

--
luigi