ANSWERS: 2
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Anapod used to work pretty well. It's not iTunes but it got the job done. Check it out, it can't really hurt. http://www.redchairsoftware.com/anapod/
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Yes, there are a few ways around it but you need to navigate through iTunes. The fact of the matter is, however, that you will simply be left in the dust in another year or two. Windows 2000 is becoming extremely outdated and you should at least have XP by the time Windows 7 comes out in 2 or 3 more years.
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