As the saying goes, bigger is better. Get the 40 GB. He'll appreciate it in the long run. I've got a couple of buddies who bought iPods before deploying to Afghanistan and Iraq. They came back with them, still looking new and working fine. So you know they're durable, lol.

I wish I had one for my trip today. All I've got is the Nike MP3 player (designed for running and other outdoor activities, no where near the amount of memory as the iPod). I could really use a 'road trip' type MP3 player though and I'll probably eventually purchase the iPod when the prices go down as time progresses.

Don't they already have 60 and 80 GB models out?