Cannot transfer files to my ipod

I have an Ipod Touch 5 that has the latest firmware.  Itunes is up to date as well.  The problem started in September after updating my ipod.  Ever since then, I am unable to transfer files.  Auto sync and manual transfer does not work.  The only thing that has worked for me is to restore my ipod and resync everything.  However, who wants to have to go to all that trouble if you just want to transfer one song?  Under "on this ipod" everything is there except they're greyed out with grey dashed circles around the songs.  I have been researching this for nearly two months without a solution.  I'm able to transfer apps just fine, it's music, videos and photos that won't work.  Please help me!

What does the gray dotted circle in...: Apple Support Communities
what does the dotted circle mean?: Apple Support Communities
Dotted circles next to songs, won't...: Apple Support Communities

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