Microsoft's Zune looks good on paper, but it's not going to kill the iPod because of three things:

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1. It's not cool and never will be. The iPod is streets ahead in the things that really matter: ease of use, aesthetics and -- here's the tough one -- cool. The Zune is not cool. You can tell that at a glance. Take the choice of colors. It'll come in black, white and brown.
Wait a sec -- brown? Surely this is some sick joke gone horribly wrong. Or are they trying to rip off LG's Chocolate phone?
The Zune's best bet is waiting it out until the iPod becomes passé, which seems unlikely given that Apple is constantly redesigning and refreshing the device.
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2. The Zune will be locked down tighter than the queen's knickers.The Zune's interesting features -- Wi-Fi sharing and the music subscription plan -- will be subject to a strict digital rights management scheme, and given Microsoft's reputation in this area (PlaysForShit) -- I'll bet the Zune will drive customers to the iPod.
After all, PlaysForSure is such a technical and marketing disaster Microsoft is abandoning it altogether in favor of the Zune, which will attempt to tightly integrate hardware, software and services, just like the iPod.
But whereas Apple's FairPlay digital rights management scheme seems to be working very well (surprisingly, there aren't widespread reports of glitches and problems), Microsoft's penchant for complex and glitchy verification systems bode ill for the device.
3. Wi-Fi song sharing will not catch on in public.The Zune's only original feature is Wi-Fi song sharing, which will allow Zune owners to search for others nearby and temporarily trade songs over the air. Traded tunes will be playable up to three times over three days, and can be flagged on the player for later purchase online. Otherwise they disappear.
But while it's obvious that sharing songs will be fun with friends at school or college, it's not an activity that will take off in public. It'll largely be confined to peer groups.
How do I know this? Because that's what's happening with iTunes music sharing, which does more or less the same thing with a computer over a network, instead of peer-to-peer.