I purchased songs on itunes

www.limewire.com is an illegal site so go out and buy the cd and then transfer them.

Try this. We had this problem too and ultimately scraped itunes and went to www.limewire.com .
Burn you purchased songs to disk and then download the files to your device or just download limewire where all songs are Mp3 formatted and it is really user friendly. Download, highlight at lower screen at limewire and hit explore - then save file to mP3 device (just be sure to always highlight target song) and it is really easy. Good Luck and Have Fun!!!