I tried that and hated it. Anapod sucks, it's unstable, you have to buy it, and it's not nearly as easy to use as they would have you think. Try Winamp + ML_iPod plugin instead, it's the only way to go.
I found a great program that will end your itunes miseries. you can drag and drop your tracks by windows explorer.
So anybody thinking twice about not getting the ipod because of the software...visit http://www.redchairsoftware.com/anapod/

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