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I would have to say that comparing the upgrade of my Zune to the upgrade of my iPod Classic, the Zune was much easier and faster.

Whats even better, is I now have a 2nd generation Zune, and I didnt have to buy it. All I had to do was upgrade my 1st gen. This is a feature iPod hasnt even dreamed of. Imagine taking your old iPod, and making it into a new gen.

Oh, and the WiFi Sync is pretty cool too. Another feature the iPod lacks.
 
Why is this in the iTunes and iPod discussion board?

Because competition is good. =)

The upgrade process wasn't without its quirks, but once it's done I'm forced to admit that the new Zune software is a huge, huge improvement over the abysmal original product. In fact, for the simple task of managing the player, it's quicker, snappier, and less kludgy than iTunes PC. The new player interface is also a big leap forward - easier to view, nicer to look at, and yet much more responsive than the original. I'm quite happy, other than the fact that the darn thing still insists on converting mp4 video to WMA in order to allow the Zune to play it.

Still, if Microsoft can continue to improve on their products at this pace, Apple is seriously going to have to start watching their tails.
 
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