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My kids use iTunes with their iPods and I use the Zune software with my Zune 30GB. I wouldn't say that either of them are particularly friendly (the software) but I have used both and don't see that either of the desktop software suites is way better than the other. The Zune software integrates nicely, though, with the Marketplace. Not familiar with the online portion of the iPod.
I'm looking forward to see what improvements are coming on 11/12 or 11/13 with the Zune firmware and software. Should be interesting.
Once set up, though, the Zune is excellent. I haven't seen the video iPods as yet but, as was mentioned, the extra feature like FM radio and bigger screen push the Zune a bit above the iPod as far as I can tell.
-CB
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