ITunes does not work in the slightest

iTunes will not allow me to place music on my iPod which I payed out the nose for. It worked perfectly until recently, when it stopped for no percievable reason. Whenever I place music onto my iPod by dragging it over to devices, iTunes says something along the lines of "determining tracks to sync." I then go to "On this iPod" and the music is there, but in a light gray font and with a dotted circle to the left of the checkmark. It goes without saying that iTunes has not even tried to actually put the music on my iPod, which is the one main job it has been designed for for over ten years. I have tried an incredible number of combinations of checking "manually manage music" and pressing the apply and/or synce button and trying the same thing over and over. None of it has worked in the slightest. Does anyone have any idea about what this could possibly mean?
This is what the song looks like in the "On this iPod" section

Try:
what does the dotted circle mean?: Apple Support Communities
What does the gray dotted circle in...: Apple Support Communities

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