have you thought about a step by step help system within Joomla! itself? I mean to distribute Joomla! packs with help as content (not in the admin or the admin screens), something like having the othermenu populated with general Joomla! concepts and changing marketing specific articles by quick guides.
I am not sure but the new help system will have contextual pop ups. That´s a great step. Another one would be to make simple guides available once Joomla! is installed. Other CMSs have them or are working on it. IMO it´s better to see, ie, the Anna´s Joomla! tips than the "If you've read anything at all about Content Management Systems (CMS), you'll probably know at least three things..." article.
PS: of course under CC a-nc-sa-wyw license. Just kidding, it´s an obsession, lol. Eppur si muove
