Why would itunes let you do that? Everything you bought is fairly low bit rate and copy protected. You would need to remove the copy protection off the tunes on your computer then use third party sync software to load them on a different device.

If you buy the CDs then rip them with something other than itunes yourself you can pick your bit rate an not copy protect them. They would be yours to do with as you like.

By the way, while the tunes are copy protected you can lose all your music and have to repurchase them. That is not unusual. People want to remove the DRMs after they lost their music. That is not possible you can only remove them while they are playable.

iTunes will let you copy the same song on to 2 different ipods???? I will believe you can have two ipods with different tunes on each.

Chewbakka sounded like wants to put the same music on both maybe I am wrong. He wasn't very clear.