ITunes or No iTunes

This may be a backwards question. I couldn't find any answers by searching the forums, so here goes. I'm looking to buy an iPod or other mp3 player for my nephew. He has some legally purchased and some illegally downloaded mp3s. I've been the good uncle and discussed copyright etc. with him. Can he transfer both legal and illegal mp3s from his iTunes? It's an older computer, like mine, that we gave him, and he has iTunes 4.7.1 I have seen all the problems with iTunes 7xxx, and have recommended he not upgrade to that. I saw in the specs for the Apple Shuffle it "requires"(?) iTunes 7xxx. What are my options?
Thanks in advance. pbb

Technically there is no barrier to using an illegally-downloaded MP3 on any system or player (presuming, of course, that there isn't a problem with the track itself). Morally it's a different story; if you know the track to be obtained illegally, then ethically it would be wrong of you to assist someone in using the track. But that's up to you.
he has iTunes 4.7.1 I have seen all the problems with iTunes 7xxx, and have recommended he not upgrade to that. I saw in the specs for the Apple Shuffle it "requires"(?) iTunes 7xxx. What are my options?
You have no option. Current iPods require a current version of iTunes. But I've been using iTunes 7 on multiple computers and never had a problem. If you're going by the posts here, then don't overreact. These forums are for technical support, so by nature what you're going to see are problem reports and so get a skewed viewpoint since those having no problem have little reason to post in a technical support forum. The chances are good, presuming the computer meets the minimum hardware and OS requirements for iTunes 7, that you'll have no problems.

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