Robert Scoble writes that although the Zune has an advantage in software extensibility — it's easier to update Zune software and there's a chance an update could give it some PDA and GameBoy-esque functionality…
But, for now, I’d stick with an iPod. Microsoft hasn’t given us a
killer feature yet that is easily demonstratable for why we should buy
a Zune instead of an iPod.
I agree with Scoble's assessment: Zune's WiFi-based song-sharing and XBox integration just don't have enough “oomph” to be considered killer features, it lacks a distinctive conversation-maker like iPod's white earbuds, nor does it have those little UI features for which Apple is famous.
There's also an issue that doesn't show up on features list comparisons: the iPod is just plain cool. While Microsoft's “consumer” offerings make you feel as if you're eating the table scraps of the people they love most, their “enterprise” customers, Apple products are like “Vince” from the HBO television series Entourage — the cool friend, who by letting you in his posse, makes you cool by association.
Here's an observation from the recent Ajax Experience conference. Although the conference organizers could've chosen to go with a more “cost-effective” MP3 player to include in the swag bag given to every attendee, they went with the iPod Shuffle. They held a number of raffles throughout the conference and a big trivia game at the end, and although they could've saved some money and handed out cheaper players, the prizes were iPod Nanos and iPod Videos. The vendors in the exhibit hall did the same: their prizes were also Nanos and Videos. There wasn't a non-Apple MP3 or video player offered as a prize, because it wouldn't have fit in with the high-end feel that they were going for with this conference.
That's why the iPod is still the Wonder Glove Monkey.