Use iTunes with *ANY* mp3 player
Many years ago, I bought an iBead Jens of Sweden MP-100. At the time I was a Windows/Linux user and everything was fine. Now that I'm a Mac user, syncing tracks to my trusty USB mp3 player is a bit harder. I had to copy tracks by hand, and when two tracks had the same title the copy would fail. THis was all very irritating. I am saving for an iPod nano, but until I get one I'm stuck with the USB copy tricks.
But not anymore, 5 minutes ago I discovered SyncTunes, a free Mac OSX application which can sync iTunes playlists to any drive as long as it's available on your desktop. This means that any drive that mounts as a removable drive (USB memory sticks, PDA's, Sony PSP's...) can be used to sync the playlist to. The only catch is that you have to make the playlist fit onto the drive (in size). This can be easily done by creating a smart playlist in iTunes which is limited in size.
I tested syncing some of my playlists (through a size-limiting playlist) and it works like a charm. Size limiting playlists are also the thing to use if you do have an iPod, and want some control on how many space is used by pop music, and how many space is used by rock. I'm a happy camper now, and in no hurry to buy an iPod (but that 8GB red nano sure looks tempting).