ITunes shows added music but won't play

Hi,
I recently started having problems with newly added mp3's to my iTunes library.  iTunes appears to have added the song to my library, as it shows up in the recently added playlists and music tab, however when I click to play the song, it skips to the last song that was successfully added.  The issue is not limited to just a single mp3, it's won't allow me to properly add any new music at all now.  I checked for software updates, and I'm running the latest version.  I have also restarted iTunes, my Macbook Air and attempted adding new music with iTunes Match turned off without any success.  Anyone else experiencing this problem?
Thanks!

I bought my wife a iPod Nano. It was sent back to Apple. I visited Aplle Store Genius' multiple times, and even got it exchanged, giving up the oringinal engraved one. Yes, it has the problem of not playing purchased Itunes songs, but it will work for while, then start skipping those purchased songs, then for no reason, starts working again! No one has any idea what to do. It has to be something with the software since this is Nano #2. I've tried everything that has been recommended. The fact that it is intermittant is the bigget mystery of all. I just turned it on and its working. When we try it later, it may not. Any ideas that any one has will be appreciated. Thanks

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