Is Wikipedia succeeding in its aim of becoming a high-quality, free encyclopedia? Or is it failing beyond all hope of recovery?

Is the mere fact that it exists on the scale it does an indication of success? Does the redistributability of its content ensure that, one way or another, it can never fail? Or does the malignant outcome of a few webcomic AfDs and the decision to make things difficult for spammers mean that the entire project is the birthchild of Satan, as many bloggers would have us believe?

Does "Featured article" status have any real meaning? Does the ratio of featured articles to non-featured articles actually tell us anything? Or is it about as useful as dividing a contributor's edit summary usage by the number of Portal talk edits they have? What about "good articles"? Is "good" good enough? Is it too good? At the end of the day, does it matter what an article is labelled as, provided it's encyclopedic and useful to its readers?

Is Wikipedia's aim to become "Britannica-or-better" quality hopelessly unattainable? Or, given that most of the Micropædia articles are a couple of paragraphs long with no authors or references, and the Macropædia has only 700 articles, has it already been attained? Is 6,789,962 articles too many, or too few? Is this metric a misleading one? What about the average length of the article? Average number of edits? Median number of minor edits per page move? Which is better – lies, damned lies, or statistics?

How reliable is Wikipedia? Has the number of elephants tripled in the last three months? If I pick a random statement from a random article, will it be true, or will it be truthy? Is it appropriate to cite Wikipedia? Is it appropriate to cite any encyclopedia? Is it appropriate to rely on anything in Wikipedia at all, ever? Do thousands of graduate students owe their degrees to it nevertheless?

Is the unevenness of Wikipedia's coverage unacceptable? Does it matter that The Banker (Deal or No Deal UK) has an article but aggregation technique does not? Is someone going to go and write that article now I've linked it? Is the overwhelming presence of popular culture and underwhelming presence of 17th-century Dutch art a poor reflection on the user demographic and an indication that we are drowning in cruft? Or is the creation of a large, centrally-organized, well-written, sourced, encyclopedic collection of information something we should consider an achievement, regardless of the subject matter?

Is RfA broken? Is it not broken? Does this have anything at all to do with the encyclopedia? Is ArbCom broken? Does this have anything at all to do with the encyclopedia? Is AfD broken? Does this have ... well, it does, but is it a problem?

Is Wikipedia confusing to newcomers? Is it hostile to outsiders? Perplexing to those not in the "inner circle"? Do experienced editors give the impression they don't care because secretly, it's just as confusing for them? Is it impossible to add information to Wikipedia without the "abusive mods" removing it? Or is this a misconception derived from the experiences of those with extreme viewpoints who attempt to rewrite controversial articles without discussing the matter with other users? Do we really care what someone who blanks an article and writes "penis" thinks of the project anyway?

Are all our articles written by high-school kids with no knowledge of the subject? Is this a bad thing? Or has Wikipedia inadvertently done something rather impressive – taken the millions of kid-hours of spare time that these people would otherwise have wasted on video games and MySpace, and actually put it to productive use? Is the project run by abusive, power-mad adolescents? Or is this an unfair generalization from the inevitable disruptive few? Is it really worth it when editors, driven mad by content disputes, threaten to climb the Reichstag dressed as Spider-Man? Is there a cabal? If so, does it exist? Can I be in it?

Is Wikipedia about to run out of funding and close down? Or did the accountant miss a zero off the last fiscal report? Will the Foundation discover $1,000,000 down the back of the sofa some time in the next four months? Or will we have to resort to running ads on Wikipedia? Would it be in the spirit of the project to do so? Would it be idiotic not to do so? Would the benefits outweigh the drawbacks, or would it drive everyone away? How much of the money would I be getting?

Does any of this matter, in the grand scheme of things? Or does Wikipedia's massive user base mean that, short of drastic action, the project will find its own direction? Would it be better if, instead of writing these essays, we wrote more articles?

Questions, questions, questions. Feel free to add more perplexing questions that no two people are ever going to agree on as you see fit.

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