Improving the newcomer experience
Two immediate problems: impenetrably confusing help system/files, and politically correct despotism in enforcing consensus over facts and good grammar.
The single most important change that can be made to ease the newcomer experience is to rationalise and condense the bewildering and shambolic help file system. No topic is ever contained in a single location - not even summaries and then links to progressive granularity of detail. Searching the help files is counter-intuitive, throwing thousands of irrelevant results back at you unless you already know what you're looking for by its precise, inevitably Wikijargonised name.
Worse, the repeated mentions of using common sense, of Wikipedia not being a democracy, and about being bold in taking risks come to naught when well-intentioned but authoritarian 'senior' editors act as some kind of Wikistapo in enforcing consensus when what's at issue is fact or grammar, which have their own internal rules that are not subject to democratic votes, or to a corporatist consensus model that has more in common with fascism than the quest for accuracy and excellence.
A case in point: trawl through the growing number of articles about Soviet history, especially those rated Good Articles, and tell me truthfully whether the standard of English used in most of them isn't appalling, and the tactics of the more petulant, precious authors in presenting their own particular sources to the exclusion of carefully referenced alternatives aren't ideologically repugnant. And yet 'experienced' Wikieditors stave off dissent and approve these articles as good examples!!!
It seems to me that rationalising help content is a purely mechanical task that should be easy, if time-consuming, for a group of serious contributors with some experience in information management to undertake as a special project.
The second problem I describe, about despotism, does not have as easy an answer. The level of politically correct, ideologically driven, concessions to special interests comes at the expense of pluralism: it is often the case that multiple, possibly conflicting sources may be necessary to provide accurate information. To demand pedantically that there is only one way of interpreting events and actions, particularly overtly political ones, is to undermine neutrality. And finally, to allow ungrammatical expression and language so ungraceful it wouldn't pass a high-school exam is to ignore that the less clear language is about intended meaning, the more likely it is that the author can deliberately or inadvertently distort meaning, and therefore even the intentions of those refrenced in citations.
If senior Wikipedia editors are so beholden to warm and fuzzy good intentions in surrendering to demands for publication and 'promotion' to GA or FA status that they can no longer recognise absence of clarity in written English, Wikipedia is irreperably damaged. The solution? Less enforced consensus (ie despotism) by those who think they know better, and more attention to rationality of argument and contribution. Rule books are good indicators, but can never replace rational assessment under specific circumstances. Peterstrempel 03:35, 16 March 2011 (UTC)
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.