We've never had the need to carry music with us. If we go somewhere, we're happy to listen to their choice of music. If we go to St. Barth or any other destination around the world, we rather listen to the local sounds (or lack of them). No need to have background sound everywhere. Walking on the beach with an iPod is the last thing we'd ever want to do.
Our music library is about 20,000 songs and takes 550 GB, all Apple Lossless encoded. It wouldn't fit in any iPod classic and in reality our music taste changes frequently so it's easier to carry a smaller iPod that is synced to exactly the music we want to listen right now. Kind of hoping that the USB cable sync stuff would eventually end and be replaced with a WiFi sync..