I know iTunes is shit, it doesn't take a law degree to figure that out. Which is why I don't use it, it's not exactly that difficult to switch to foobar, MediaMonkey, WinAmp, whatever you like. AAC files never even come into the picture.
The iPod, on the other hand, is a miracle of industrial design and is so laboriously intuitive that it's almost idiotic to try and write it off as a "conformist cliche". And this is coming from a guy who hates Apple (Macs are shit too, by the way).
Why try to derail a thread that's clearly productive? We all know you don't listen to sacred cows (apparently something you pride yourself on), what reason would you have to get offended by someone offering their own hundred-song list? How is this any worse than the hundred-albums list that people spread around?
In the immortal worRAB of the OP: