How do I sync music from both my mac and pc?

Okay...here is my problem.
When I bought the first ipod all the music went on my pc. I then bought a second ipod and, using the same account, bought other music on my imac.
Now I can either put the music on my ipod from the pc, or the mac, but not from both. When I try and sync the two, 30 of the songs say they won't transfer.
Any solutions?
Thanks!

Maybe you should switch from auto sync to manually manage music. Then you can click and drag the items/playlists from either computer to the iPod when it's connected.

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