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The "pain" is a one-time process; I suspect that most of us who are long-time iPod users have forgotten the initial hassle of it all.
Strange that iTunes wouldn't run on your PC, Nate. I've installed it on more machines than I can remember, and not had a problem.
But yes, "locked down" is the price you pay for buying Apple kit. That's why I don't use my iPod Touch as a book reader; it's just too painful to get books on it. Music and video are a lot more straightforward.
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