good luck with all that, i had 2 ipods on the same itunes and it worked 40pct of the time max. apple suport suggested rebooting, which i had to do frequently. it also caused problems when u have more than one person logged into your computer at once. they make it so difficult to do simple tasks. i now use drag and drop from windows explorer from my sansa. this way u can share as much music as u want with anyone