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iPod Touch ($199, 8GB) -> Zune HD ($219, 16GB)
I know, I know. Why buy a Zune? If you're heavily invested in iTunes albums, the answer is, no reason. But for those who are willing to break from the Apple music infrastructure, the Zune HD is actually an awesome PMP. The aluminum case is very sharp, with an OLED screen that's richer than any iPod (though slightly worse in the sun). The Zune software, coupled with optional unlimited download subscription packages, is every bit as hip and convenient as Cover Flow and iTunes, provided you run Windows. Oh, also, you don't need to drop $300 to get a decent amount of storage and you get HD TV-Out and a not-so-bad TV interface to boot. So when you're sick of the little screen, you can go as big as you'd like.
What you gain:
• 8GB more storage (base model)
• HD Radio
• Unlimited music subscription with free MP3s
• HD TV-Out and an on-screen TV interface
What you lose:
• iTunes integration
• About a billion apps
