Voted.

From the UI documentation side of things, it's difficult to keep them up-to-date due to the fact that the client is still under very active development and things are changing regularly.  An idea that popped into my head would be the ability to be able to "tag" elements within the client with UI hints that could be then used by a selenium-driven tool for automatically generating new screenshots with the appropriate outlines/highlights.  Obviously this would not be able to cover all the cases, but perhaps it may be worth the time -- or someone has already written enough of a tool that we'd be able to piggyback off of?

As is the case with most open source projects, documentation tends to be the most neglected.  While I'm more than willing to help with writing technical/UI documentation, I'd also love to get involved with some tooling to help automate what can be automated so more time can be focused on improving that which can not be automated.