Probably the most sensible solution. Thanks. (I hate supporting what I think of as an ultra-closed system, but you're probably right. It's not like I'd be murdering someone, just buying an iPod. )

But if anyone else has info to add on getting music and other files out of an iPod, I'd be curious.

(A little later ... ) In light of Gerbick's post about moving iTunes songs to his Zune, and Totololo's comment about AAC-compatibility, I looked at NewEgg's mp3 players with a filter for only AAC-format-playing units ... They list 79 units, but only 3 units under $100 played AAC, and two of those were recertified Zunes.

Then I looked at making iTunes play nice with other mp3 players. And it looks like a pain. There's iTunes Agent and BadApple, maybe others. For me, I'd do it. But an impatient teenager isn't going to. Besides, it looks like if you really want to go that route, your life would be a lot easier if you had iTunes encoding as mp3 to begin with; I'm sure he did what Apple makes easy, used AAC. Finally, it appears that the only way to get an iTunes-store-purchased song to play on a non-iPod (or non-AAC) player is to first burn it to CD, or use software that makes your hard drive emulate a CD disk (like NoteBurner). What a pain.

This bit of research confirms what I had to say in my posts about why I can't recommend a NIT to my friend and how Nokia and all the other non-Apple companies in this space are really starting out from way behind. I think I won't get the kid any MP3 player at all and use the money to buy him a share of Apple stock!