Ben, many mp3 players work with Macs but don't have automatic synchronization. The player would appear as a disk, and David's son would have to manually move songs on to and off of it, but it would certainly work.
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David-
First of all, welcome to Discussions and to the Mac world.
I'd say "go with the iPod." I'm not just being an Apple supporter.
As I said above, there are many mp3 players that you'd be able to hook up to the iBook without a problem, but
managing music on one (especially at higher capacities) would be annoyingly difficult. Apple's iTunes software, which comes with the iBook, has great built-in support for iPods, so your son would have the easiest time with it. I haven't heard of other mp3 players out there that come with Mac synchronization software, but I might be missing them.
That brings me to another point. You said that you want to get him the most storage you can afford. There's much more to an mp3 player then that. iPods cost more mainly because they're easy to use and have that great sync ability. People just tend to be happier with them. And if he has already asked for one, he might be happier with an iPod of lesser capacity than a large player that would be more annoying to use in everyday life. There are many
models of iPod, from the half-gig, $99, screenless Shuffle to the 60 GB, $399, video-playing iPod. I personally like one of the newest, the nano It's unimaginably tiny.
I'm sorry if I sound like an Apple sales rep! I'm not; Apple's products are just easy to love.
Whatever your final decision, good luck.