Putting my music on a friend's nano

Here's the deal - A friend of mine has asked me to fill his nano with music of mine and I have a couple of questions to avoid any sticky moments:
1. To load music I will have to synch his nano to my mac's iTunes, but he has a pc. If I strip his nano and then add music, will he be able to synch it to his iTunes on a pc? Also, assuming that can happen, what will he need to do to transfer these purchases?
2.  DRM. Will I be alerted bu iTunes, should there be any DRM issues with albums I attempt to transfer?
BTW, currently I do not know the gen of the nano, my friend is not tech savvy and has no idea.

I'm pretty sure that if there are no DRM issues that I he will not be stealing, rather I am giving.  If there is an issue, then he will be unable to receive the music. Thank you for your input

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