Update: The link to Why Craigslist is such a mess!
September Wired Magazine's "The Tragedy of CraigsList" (not yet online) by Gary Wolf calls the popular site "firmly stuck in 1999" saying its main failure is refusing to evolve.
Similar to a 2006 SXSW panel, Wired proposes five mostly serious alternative designs to improve the site.
I'll give a few brief excerpts but to read the article, you'll either need to buy the issue or wait for it to appear online:
Craig Newmark started a galactic garage sale with millions of users, a killer business model and revenue to match. So why is the site such a wreck?
Internet's great promise is to make the world's information universally accessible and useful. So how come when you arrive at the most popular dating site in the US you find a stream of anonymous come-ons intermixed with insults, ads for prostitutes, naked pictures, and obvious scams? In a design straight from the earliest days of the Web, miscellaneous posts compete for attention on page after page of blue links, undifferentiated by tags or ratings or even user names. Millions of people apparently believe that love awaits here, but it is well hidden. Is this really the best we can do?
Revenue from newspaper classified ads is off nearly 50 percent in the past decade, a drop that comes to almost $10 billion. Only a fraction of this loss is because of Newmark's company, but as the largest online classified site, craigslist is easy to blame.
Because he is the founder of a remarkable Internet company that also happens to be helping the nation's dailies go out of business, Newmark's opinion is eagerly sought, and he spends an increasing amount of time at conferences and international meetings, where he attempts to answer questions about how to best defend the public interest in an era of cheap and ubiquitous media. As we watch the birds on the patio of Reverie, Newmark tries out some of the phrases he is hoping to use in the coming months as he unfolfs the lessons of craigslist. "My big mission is to help make grassroots democracy as much a part of our government as representative democracy," he says.
I'll link to the full article when it is available online at Wired.