Join Date: Jun 2007
Location: Marin, California
Since iTunes shifted to DRM free content, your player should be able to play anything you purchased after the switch. If you go to the iTunes store and click on "Upgrade to iTunes Plus" on the right hand side it will allow you to "upgrade" your older purchases to DRM free purchases. I'd upgrade 1 song then copy to your player and make sure it works before you go any further. Copy from the iTunes folder in your "My Documents" folder and you should be golden.
07 Magnetic Blue Exige S
"Mostly though, it's just a triumph of British engineering." -Jeremy Clarkson