Discussions of context on the Web tend invariably toward Wikipedia. The site is a wondrous exemplar of the radical new ways in which information can be created and structured after we’ve cast off our legacy media forbears.

And yet.

What Wikipedia lacks in beauty, it makes up for in ugliness. The editing interface is hideously unfriendly. Discussion pages – while often fascinating – are a hot mess. There’s no easy way to satisfy the audience desire for both overview and update; if Wikipedia introduces you to a subject, it’s often a poor place to follow that subject as it develops. And the site emphasizes comprehensiveness over synthesis – you wouldn’t go to Wikipedia for a concise introduction to the challenges in U.S. immigration policy, you’d look to it for a thorough history of everything there is to know about the subject.

Elsewhere on the Web, we haven’t seen much evolution beyond the model of the wiki set forth by Wikipedia. Wiki markup everywhere tends to be unintuitive at best. Templating for wikis is a nightmare. And they haven’t yet developed the type of storytelling variety you see in blogs, which have now evolved tumblelogging, microblogging, photoblogging, videoblogging, audioblogging, and more. Few people are yet using wikis to create content that is strikingly visual and concise. It’s certainly possible to create a wiki that’s attractive, but it’s quite an undertaking.

The ideal wiki technology would make it possible for a community to create and maintain something like The Money Meltdown, and one day, perhaps even The Bold Italic. It would enable you to easily link episodic and comprehensive information; for example, an update to the wiki could be tied to a blog post explaining a new development. And the interface would be as friendly as that of WordPress for would-be wiki creators, editors, and designers.