Syncing iMac PowerBook and iPod

Ok, here goes my problem.
a) I have an iMac at home with ... say 2800 songs.
b) a PowerBook at work with ... say 1500 songs.
c) and the Ipod with 2000 songs.
I want them all to have the same songs, BUT
without duplicating and most importantly without deleting them!
I am afraid to sync any of the three because I think that I might lose any of the songs.
Any instructions for dummies?
Many thanks,
Julio

Many thanks!
Since there are more than 1000 songs, is there a way to avoid going song by song to see if I have them on each computer?
I mean, I know that out of 2000 songs on each computer, at least 1500 must be the same ones. This is, I have the same 1500 songs both in my iMac, and the Powerbook. Is there a way to know or to transfer only the new songs added to my PB without exploring song by song to see if it is repeated or not?
Thanks,
Julio

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