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Why Wikipedia Can't Work
Wikipedia claims (or is promoted by its users as) a replacement for the traditional encyclopedia. They frequently compare themselves to the Encyclopaedia Britannica, but in reality Wikipedia is not an adequate substitute, let alone a replacement. What's more, because of fundamental problems in Wikipedia's philosophy, design, and operation, it would appear impossible for Wikipedia to ever become such a substitute. 

There are many problems with Wikipedia, some more important than others. I'll discuss only two that have bitten me in the past. 

The Ignorant Edit-Bully
Many people have noted this phenomenon, though I've never seen a good name for it before. In a nutshell, the problem is that a person knowledgable in a given field (but not a regular Wikipedia contributor) notices an obvious error in a page devoted to a topic in that field. They want to be a good citizen, so they edit the page and correct the error. However, within minutes, their correction has been reverted, restoring the error, and if they're particularly unlucky, they may receive a note from the person that reverts their change, accusing them of ""page vandalism"". 

It seems that there are a large number of Wikipedia devotees or zealots who have little more to do than hang around the Wikipedia site, watching for edits to pages that they've contributed to. Any change to ""their"" page is taken as a personal insult and instantly reverted, regardless of its merit. What's worse is that the types of people who do this simply do not have the knowledge or intellectual tools to recognize the merit of the contribution. They would appear to typically be young people, perhaps in their first couple of years of college. They have the headstrong ignorance of the young adult, coupled with an insecurity complex that makes them unable to accept that others might have something to contribute that they themselves lack. In ""real life"" they would be harmless, as they wouldn't be able to stand up to others in a confrontation, but the anonymity and isolation of the internet give them the confidence to become overly assertive. 

So an expert makes a contribution, sees it discarded by someone who obviously has no qualifications to judge it and all the time in the world to get their own way, and the expert simply leaves, never to contribute to Wikipedia again. The quality of many of Wikipedia's articles clearly shows this phenomenon; reading through the edit history of many pages shows it in action, graphically. 

No Editors Means No Sense of the Valuable
Wikipedia prides itself on not relying on professional editors, which they claim makes Wikipedia more egalitarian. However, egalitarianism is not necessarily a desirable quality in a reference work, as the philosophy of everyones contributions being equally valuable is simply untrue in the real world. As Theodore Sturgeon noted, ""ninety percent of everything is [crap]"". 

This leads to the problem of many of the Wikipedia articles having been created or primarily edited by the ""edit bullies"" described above: 

They do not necessarily have a broad knowledge of any of the topics they write about. 
They are generally not well-read or broadly-educated, having little context for the particular areas they have studied in any depth. 
They tend to have concentrated their reading on various things of personal interest to them, so they have no sense of proportion or of what is truly significant to the world, versus the trivia that was important to them as teenagers and such 
This results in the Wikipedia in general having laughably large holes in the areas it covers, while having an even more ridiculous amount of spurious detail on subjects that it has no need to cover. My current favourite example: 

Many Wikipedia articles about important historical figures are little more than caricatures, if they have sufficient details to even be called that. Many other important figures are simply not mentioned in Wikipedia at all. A number of months ago, I looked for information on an important North American manufacturing industry figure from the 1980s; he could be considered the most important business person of the decade. I was somewhat shocked to see that there was no article about him at all. Note that I am not identifying him by name; this is because Wikipedia tends to react quickly to correct specific faults only when those particular faults are widely publicized, in order to render that particular critique null. 

So, being a good naive contributor, I created the article. I noted who he was, why he was famous, a few of his most important accomplishments, and I properly notated the article as being a people-related article stub, hoping others would help flesh it out. A few weeks later, I checked back, only to find that the article had been c