WHY FEATURES DON'T MATTER ANYMORE: THE NEW LAWS OF DIGITAL TECHNOLOGY is a great article on why the iPod caught on and what to consider when designing anything. Tools (hardware or software) are overloaded with features that people don't have time to learn.
Craig's List drives me a bit crazy. It doesn't let me work the way that I want, sorting things this way or that. But given that it's a bunch of free ads for stuff that might or might not be still available, well, OK, sorting latest first works. What's the point of sorting by make and price, then finding out that the item is gone?
And clearly the interface works for a lot of people.