Document for Usability
While documentation has improved significantly over the past, there are parts which are still lacking when it comes to usability.
Some parts of the functionality seem poorly documented because they might not be part of SilverStripe "proper" - but they are still part of what the user community needs in order to build a great site. (One area which is difficult to traverse is the gap between SilverStripe and Sapphire: after a year I still haven't found great documentation on this. Authors of plugins are also notorious for minimal documentation rather than great documentation, but I'd rather get their contribution than complain about not getting more.
Great Documentation should include a comprehensive list of options, and clear examples of using both a minimal and a comprehensive sample. Users shouldn't already have to know how to use the system in order to read the documentation.
New Documentation website at http://docs.silverstripe.org/
New documentation site has been released and a series of new lessons is actively being produced. I will close this item out as it is more general. If there is specific documentation you'd like to see request this as a distinct uservoice item so we can more easily break the work down and get people contributing. :)
Thanks Paul, I agree documentation needs work. There has been a good discussion about this at https://groups.google.com/forum/?fromgroups#!topic/silverstripe-dev/3X8kZVSqPiY and some work is actually underway on this.