More than likely not to be honest. I know that anything bought from iTunes Music Store can be licensed to 5 computers at a time but I don't think that goes as far as 5 non-family members with a computer each.

I'm also sure that technically ripping a CD into iTunes has grey-area legality and even if the resulting M4A/MP3/AAC files are legally OK they're not going to be re-distributable.

But let's be honest, how is anybody going to know? I'd be more concerned about the iTunes library sync issues with having your iPod linked to his library, unless you use the hard disk capability (of the top-end models) to copy files over as files and import them into your own iTunes.

I guess it comes down to your conscience...

MOU
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