A friend of mine bought his first Apple product: iPad 3rd gen.
He's a professor.  At the university he has a desktop PC.  He also has a PC laptop which he uses mostly at home or on the road (though he's doing his best to see if his iPad can replace his aging PC laptop - and by and large, the iPad is doing quite well: he pulls student papers remotely from his office PC, edits and annotates them,  sends them back over a VPN connection, uploads them to Dropbox, distributes them to other professors and students etc).

The problem is with his music library and getting syncing with his iPad.

His office PC has a bunch of tunes ripped into iTunes from CDs and a sundry of tunes he had purchased from non-iTunes sources.   

He's discovered that iTunes is not pushing all his tunes to his new iPad when syncing.  

At first, I figured it was a file format and/or DRM issue.  

But it turns out, and only for some albums that have been ripped, some of the tunes never make it on to the iPad.

He can PLAY these non-transferred tunes just fine within iTunes on his Desktop PC, but they just don't get moved to his iPad when syncing.  Repeated syncing didn't help.  Sometimes, he gets an alert saying the files can't be found.

Frustrated (particularly since I encouraged him to get an iPad and move to the Mac world where things "just work"), he tried syncing his library against his PC laptop.  The same thing happened, but in some instances, a few more tunes (related to full albums) actually got moved over.  

I asked about his iTunes preferences on his PCs, and specifically, about the following:



I have mine turned ON.  He has them turned OFF.  

I assume this means his actual media might be strewn about his Windows file system and causing the sync issue or forcing the alert saying the songs can't be found.  But that doesn't explain (or doesn't explain well) why the iTunes app on his PC *can* play these problematic tunes just fine, ie: it knows where they are, but when syncing, it doesn't know where they are. 

I'm not sure how to help him.  I would think he should recreate his iTunes library from scratch with the above preferences turned ON.  However, not knowing how his medias is stored on his PC (and having not used a PC in ages), I am hesitant to tell him to delete his iTunes Library and start over fearing he might lose his media if not his mind.

Thoughts? suggestions?
Thanks,
Kevin





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