iPod Shuffle Tip Caveat
Okay, so this comment is eight months after the OP ("iPod Shuffle Tip" by Jason). If you follow the recommendation to downsample your files on-the-fly while tranferring them to your iPod Shuffle, expect to chew up a lot of processor time. If you happen to have a 350MHz G3, don't even bother--it'll take hours and freeze up your Mac.