So I Have To Ask....

I have never heard of that happening, but I would send your friend to Apple's web site. Search the Windows iTunes support and the forums. If they don't find an answer then they should post the question to the iTunes forum, some real savvy people hang out there.

My 2nd Gen iPod has not been sync'd in months and still works fine. Of course, I am on a iBook G4.

This has happened to my son's iPod Mini as well. He rarely connects his to the family PC, and there does seem to be an issue with purchased songs not playing after a period of time.

I have looked at Apple's forums in the past - a few months ago - and the solutions proposed do not work (they generally involve resetting the software update on the iPod). If you find a solution or hear a reason I'd love to know about it, actually.

I have an iPod photo that has many songs purchased from the iTMS. I have gone for several months without synchonizing yet have never had a problem playing those songs.

I have a Mini and this has occurred to me frequently. I assumed that it was a copyright protection feature to insure that I really had purchased those songs. They all work fine again when I sync to my Mac, so I never really worried about it.