When I first looked at iTunes (for Windows) I hated it instantly. That might have been partly due to the fact that my media files were all organised fairly carefully already, and it seemed to want to go ahead and fuck about with all of that despite my protests. After having a play about with it, and failing to see the appeal, I uninstalled it and went on with my life.
However last night I set it up for someone non technical. She insisted on iTunes, so I didn't argue, and while installing it I got an insight into how it has a lot of features which would appeal to people. Importing CDs was a simple click - obviously no control as to how the files are named, no dialog boxes for encoding formats and quality (although those options are obviously there in preferences for those who care to go looking for them), you just click and it does it.
When it comes down to it, I like to know where my files are physically located. I don't want to be chained to any one program, and by having a directory structure I can obviously play my media files in any player I choose at any time, with no problems - iTunes offers a lot of convinience for people who don't want to understand those sorts of things, they want to believe that their CDs are "imported into iTunes" instead of needing to grasp the reality of what's happening underneath, and therein lies the magic of iTunes. Things like encoding CDs to MP3s (or ATRAC -_-), burning CDs, or simply using digital media in general used to be things that belonged in the realm of only the IT savvy, and it's programs like iTunes which are changing that and making technology more accessible. These are all good things, however they're also the reason why the program simply does not appeal to me.