Synching question (5th Gen late 2006)

Friend gave me an iPod 5th Gen late 2006 (so called 5.5) - 30GB.
Seems to work OK except when I synch.
Sych operation only copies 140 songs of a couple thousand (17GB).
Any ideas why?
Mac 10.8.4
iTunes 11.0.4
iPod 1.3
All music is "watched" - stored in iCloud.
Thanks for ideas.
HNick

Hi HNickM,
Thanks for visiting Apple Support Communities.
You may find the steps in the iPod troubleshooting assistant helpful:
http://www.apple.com/support/ipod/five_rs/ipod5gen/
Cheers,
Jeremy

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