Improving the newcomer experience

Wikipedia's help files are the best I have ever seen for any comparably complex system. I'd be curious to know what you are comparing them to. Reading them is hard work, to be sure, but what other comparably complex and powerful system is any easier to learn? To see some dreadful manuals, browse through the Comprehensive Perl Archive Network.

We can always make Wikipedia's manuals better. Anyone is free to write the "summaries and then links to progressive granularity of detail" you suggest. We might make the manuals easier to search by recording the search keywords that new users try when they are trying to find some wikijargonized topic whose name they don't know yet. On the Help desk, for example, I've noticed that questioners seem to use every word but "article" when they mean "article" (such as entry, profile, topic, file, wiki, site, ...). We could embed lists of keyword synonyms on our manual pages to make them visible to search, but not visible to readers which would encourage synonym disease.

Have you seen The Missing Manual? Unlike the manuals proper, that book provides a structured introduction to editing on Wikipedia.

I agree that exhortations to boldness, when directed toward newcomers, produce the same results as we saw in the opening battle sequence of Saving Private Ryan in which soldiers boldly got chopped to bits by machine guns. Boldness should only be in proportion to one's knowledge of the arcane rules.