Hi Terri,
Do you have a large music collection or a small one?
If you have a large collection, I suggest making a playlist of the songs that
you want to sync, then sync that playlist.
If you have a small library, then checking each one wouldn't be bad.
To get you started, assuming you want to
Somewhere in iTunes there is a setting to sync all songs in a selected
folder. This was how I ultimately solved the issue of transferring and
syncing music. After that, I was able to delete songs and clean up the
library over time. Sorry but I don't recall where that option is but
if you look in