depends what media you have availible. When I switched over my songs, I just...
1) copied the files on the PC with windows explorer to DVDs
2) Pasted the contents of the DVD's in a new folder on my desktop.
3) Added the files to my Itunes library
4) Used the Itunes "consolidate Library" option in the Advanced settings.
If you have a decent network, you could just copy and paste the folder with the music from the PC to the Mac, and then follow steps 3 & 4.
And as far as the ipod goes, just deselect the autosync option.
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