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My experience with the iTune/Ipod thing has been limited and varied. My sister-in-law has an 8 GB model (must be a nano) that she asked for help with on loading/setting it up. What I found out quickly was that iTunes will not work with win2k on any recent enough build for the newer models. I ended up using winamp (yet another audio program I was done with a loooong time ago) with the sourceforge plugin which works adequately for transferring music.
I have a strong personal dislike for iTunes for several reasons (mainly looks and feels like a bloated pig to me without proper audio codec support compared to Foobar2000) but I did try to install it on my winXP.
My overall impression - nice looking player after I fixed the random white screen of death, but the godawful software and too narrow codec support would push me elsewhere if I was buying an uppity fancy one anytime soon. Ogg-Vorbis and FLAC support if possible are more important to me personally along with a good working interface (which Apple does excel at).
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Started talking to yourself I see.
Yes, it's the only way I can be certain of an intelligent conversation.
Black Adder
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