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Oct 3, 2016 8:44 AM in response to Ruby318by turingtest2,One possible cause for repeated syncing of the same content is duplicate entries in the library for the same set of physical files. See Re: Every Single Song in iTunes 12.4.3 on Windows 10 is duplicated for a post on this topic. If it isn't a duplicates issue then see Re: iTunes won't sync all my songs for a method that should clear up issues with tracks that aren't syncing properly.
tt2