Honestly? They're not that dissimilar, and each of them would probably get the job done just fine.
I have a 30GB, previous generation iPod classic and a latest generation 8GB iPod Nano. I'm very happy with both, though I really wish they'd kept the firewire option (I do understand why they dropped it). They interface with iTunes seamlessly. They load music quickly enough. The build quality is just fine. The screens are impressive. The UI is outstanding.
I've only used the 8GB Zune at the store, but it seemed to work just fine.
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