Vista won't synch

I am unable to synch my son's shuffle with his iTunes library - which we previously could do with older PC running XP2.
Background
New Dell machine with Vista, iTunes is installed (latest available version). Ported all songs from older machine via thumb drive and ordered some new ones via iTunes - all are showing in iTunes library on new PC.
Can see the iPod in iTunes, can also see the Shuffle in Vista's My Computer.
But when try to synch, it puts nothing on the Shuffle. It shows a synch happening, but nothing gets synch'd.
Help on this? If this duplicates other posts, sorry.

Play one or more of the songs from the old PC in iTunes and then see if you can load them on shuffle... it may be an authorization issue. Otherwise, take a closer look at the songs you transferred, there meay be a format/encoding/bitrate mismatch. (File>Get Info> Summary)

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