You don't have to use MusicMatch unless you're fooling with DRM music-- the Dell DJ driver will allow you to copy through a device in My Computer.
But, I'd say this decision is in the eye of the beholder, or the beholder of the wallet.
The DJ is probably the most bang for the buck, GB to dollar-wise, but I think the interface on the iPod is a little nicer. My advice would be to hit up a Dell kiosk in your local mall (if available), an Apple store, or other electronics retailer, and try them all out before making a decision.
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