I think the help files are too sketchy, and sometimes inaccurate.
I understand that Jonathan is quite busy, and has not the will/time to expand and update them.
On the other hand, I see that there are quite a few people with the knowledge and the will to dedicate time and efforts to give informations and help, both on post and on external web sites (and, I assume, on chat).
Therefore, I think that a wiki for the help files, on the model of Wikipedia could work very well.
As an explanation of what a wiki is, you can read the following article about Wikipedia, which appeared on Time magazine.
More in details, besides the current help files, there would be more pages written by various people in the community about various topics. Everybody with an account on CB could create and/or modify such pages. To keep destructive behaviour at bay, 48! people could not write.
Please add your comments, corrections and suggestions.