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I have a 40gb equivilant type player...
While I only have 12 gigs filled. I plan on borrowing lots of friends cd's....
So 20 vs 40 depends on how many cd's he has / plans to have to borrow, etc.
I'd go with the WDIL / Date, but that's just me.
Maybe put his name or his initials on it too... I wouldn't have both of your names on their though, just because it doesn't seem right to engrave that on an ipod.
and if you're ever concerned with money, if he can stand a slightly larger mp3 player, go for the Creative Nomad Jukebox Zen Extra
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