Most Help content currently originates in the IU Knowledge Base. It is exported via web services to xml format. Updates are checked in to svn in html form, by a daily synchronization script.
However, the current html format does not permit many localization requirements for help content, such as reflecting local tool names in Help pages, or even using a non-default skin. The help documents in svn therefore need to change to an xml format, so that xsl transformations can be applied dynamically on startup or as the page is served to user, to allow easy localization without needing to change the source content itself.
The Help tool therefore needs some slight reengineering to use help content in xml form, and allow a range of dynamic localizations to be applied. The Help content in xml form needs certain additional markup, for example tool names identified so that the Help tool can substitute local names on startup.
A new initiative to rethink the Sakai documentation is underway (Oct. 2010). See: http://confluence.sakaiproject.org/display/ESUP/Help+Files+and+Documentation+Process+Redesign
Various requests for UI improvements are captured in Help Requirements and Feature Requests - see Current Help Issues.