There is a significant difference between understanding something intellectually and understanding it in such a way that it becomes intuitive or second-nature.

There is a significant difference between understanding something intellectually and understanding it in such a way that it becomes intuitive or second-nature. That the task of getting the content from one place to another can be done reliably with practically no user intervention is a boon for people who don't find operating a computer intrinsically rewarding, and one of the key reasons the iPod was and is so successful among those people. Being a HN reader, you probably have enough experience with computers that the cognitive load of tasks like file management is basically zero. But for most people, even many people who use computers on a daily basis, the cognitive load involved in managing a library of thousands of files is much higher than that of simply plugging something in. Unless they have a particular motivation to favor the former, the latter is always going to be more appealing.