The following is a letter I sent to Apple's support department in regards to iTunes:

Hi, I am currently using iTunes to manage my iPod library. I have a 30GB iPod and somewhere close to 50GB of MP3 and AAC files. Obviously, I can't put all of the songs in my library onto my iPod. The problem with this situation is that I am required to update my iPod manually or via playlists. This makes it very easy for me to have duplicate files on my iPod.

I'm not sure of the best way to do it, but I would like iTunes to know when I am putting multiple versions of a song on my iPod. A possible solution could be a special playlist in iTunes that will list all of the songs on my iPod. When I attach my iPod it will sync with this playlist instead of my entire library. The distinguishing features of this playlist would be its ability to recongnize duplicate songs and its awareness of the size of my iPod. This way I would not add too many songs and there would never be duplicates of the ones I add.

As more and more people begin to transfer their music collections to digital files, this will become a bigger issue. Thanks for your time and I hope to see a similar feature in a future version of iTunes.

For those of you in the same situation (more songs in your library than what can fit on your iPod), how do you deal with the problem? Myself and a couple friends are having issues.