"Would anyone here make the argument that Craigslist would have failed with proper whitespacing, appropriate font selections, and logical visual hierarchies? Those can all be accomplished with a single stylesheet."
Many successful websites (Google, craigslist, ebay, wikipedia, myspace etc) are both highly functional and divergent from "good design practices".
What I find troubling is that I don't believe any of those sites would have been constructed in their successful form by a design professional. We don't fully understand how people's perceptions are shaped by the presentation of information.
Having appropriate whitespace/fonts etc produces a clean looking site which conforms to a very particular aesthetic which has no proven connection to the success of a site and may substantially harm it.
There's no doubt that some of the most successful sites have been pretty ugly. But to imitate the ugliness smacks of cargo cultism -- reproducing side effects in hopes of receiving a similar result. To me, the commonality shared by the sites you mentioned isn't their aesthetics, but rather that they represented either a radical innovation or a radical improvement over existing services. I DO believe this was a result of their engineering focus in the early stages, a side effect of which was poor aesthetics, but I don't think it's a clear indicator that an engineer-driven product cannot also benefit from smart design. Google's move to break the Altavista portal mode of thinking and present the user with a large, isolated search box was first and foremost a design decision.
I think Mint is a good example of design driving success. Mint is largely built on the Yodlee platform, but they made the interface their primary focus. I don't get any information from Mint that I can't get on my bank's website. But since signing up for Mint, I check my accounts twice as frequently, classify all of my purchases, track my financial history, and set budgets. I didn't have to wrestle myself into these habits, either -- they came naturally because Mint made them easy and available. And honestly, I would never have trusted my bank account information to a site that looked like early-days eBay.
Many successful websites (Google, craigslist, ebay, wikipedia, myspace etc) are both highly functional and divergent from "good design practices".
What I find troubling is that I don't believe any of those sites would have been constructed in their successful form by a design professional. We don't fully understand how people's perceptions are shaped by the presentation of information.
Having appropriate whitespace/fonts etc produces a clean looking site which conforms to a very particular aesthetic which has no proven connection to the success of a site and may substantially harm it.