Rick Todd (8/12/2009)
Hey Steve, you should get your son a Zune Pass for a couple of months and see what he thinks. Basically it's all-you-can-eat music for as long as you're subscribed. You can download whatever you want and listen to it on up to 3 computers, and (I think) 2 Zunes. Since the music is DRMed it has to be played through the Zune software or through a Zune device.
I thought about that, and might try it. He doesn't buy a lot of music (yet), so buying a few MP3s from amazon and iTunes and sharing them with him has worked well so far.