I don't think Apple is new to poor user interface design. I installed iTunes (because there was no other easy way to put music on the dumb thing) and tried to copy some music files to the iPod. What a nightmare. That was a few years ago. I remember wondering what all the fuss about the "Apple user experience" was about. It seemed like the worst thing since Windows to me.
Previously, I had used SanDisk Sansa mp3 players. They couldn't have been simpler or easier to use. Apple could have learned a lot from them, if they cared about anything but trying to extract as much cash out of you as possible.
Disclaimer: I own Apple stock (which has been very good to me) but no Apple products. Please keep buying Apple products...I'm sure the usability will improve.