Your link is 404'ing for me.
+1 for automated docs. I think our best place to start is with generated API docs. We need to document widget options and (public at least) API methods. Doing so in the code directly, and then extracting that into generated API doc would give us an almost free start on the docs. We can then look at building on top of that with a more sophisticated manipulation of the source and examples to provide more "natural" feeling documentation.
Are there any modern replacements for jsdoc for generating API docs?