This seems a great idea but not sure if it works with the latest version of iTunes.
BadApple is a free plug-in for iTunes which allows you to sync your music library to any MP3 player (not just an iPod). After downloading and installing the software, you will have a “Sync to MP3 player” link you can click on from within iTunes. This will sync all tracks to a MP3 player.
BadApple will work with a wide range of MP3 players such as the Creative Nomad, Dell DJ, Archos and more. Any unit that mounts as a USB mass storage device should work well with BadApple.
BadApple is free software that you can download here.