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It all depends on how much you would use yours. I got mine for free when I got my Powerbook because I'm a student. I wouldn't have purchased one otherwise and if I had, I would've been pissed; I rarely used it when I first got it, and I haven't even used it once this year. My mom used it when she would go jogging, but for some reason the HD crashed randomnly. So for now, it's sitting under a pile of CD-Rs on my desk.
The iTunes aspect of it meant nothing to me as the MP3s that I want to purchase are very rarely, if ever, available on it, and I was also going to be getting the program for free on my Powerbook.
Although if you listen to music often enough when you're out and about, then I don't see that being a problem for you. 
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