both a Mac and a PC

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2012 Mac Mini: 500GB-8GH : iPad 2 64GB
Not really..
When you get an iPod you have to choose if you want it to work with Mac or Windows..
Say you chose a Mac, the iPod would be formated for Mac so if you plug it in to a window the iPod would uninstall the Mac software, along with all the music , pictures and movie's.
 
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White MacBook. iLife '09. iWork '09. Mac OS X 10.6
I do believe you can add music from more than one machine (if both are on the same platform) but not sync them. Like Thatguy16 said, I doubt it's possible.
 
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Black Macbook C2D 2GHz 3GB RAM 250GB HD iPhone 4 iPad 3G
iPod Nano is correct. You can only sync with one library at a time. However, you can most certainly connect to both if you manually manage the music on the iPod. The only caveat is that you have to make sure it's Windows formatted and not Mac formatted (iTunes on Windows will format it as FAT32, which both OSes can read, whereas a Mac will format it as HFS+, which Windows can't read natively).

So to summarize, connect it to your Windows PC, have iTunes format it, then check the settings allowing you to manually manage your music. Then connect it to your Mac and check off the same setting. You should now be able to manually add music to your iPod from both computers.
 

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