Ford Sync System

Can someone please tell me what I am doing wrong. I downloaded music from itunes then copied it from my Mac to an USB stick to play in the USB port on my Ford's Sync System. I can only get five or six songs to play out of around thirty. I then tried the same procedure through the Windows side of my Mac with the same results. Would appreciate any help.

Are all the songs in question "iTunes Plus" songs? (i.e. - DRM-free)
If the ones that will not play are "regular" iTunes songs (no plus sign) then they probably will not play on the Ford system due to the FairPlay DRM scheme required by the record labels.

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