iPod Nano 3rd Generation not syncing up with itunes

My 3rd gen iPod (ancient history I know I know, but I am sentimental) will not sync new songs / purchases from itunes even though I see the purchases in my library / have receipt of them being purchased. I have a PC so I am curious if there is one issue alone or if there is a variety of issues. iTunes is updated to the most recent version, PC is uploaded appropriately too. When I run diagnostics it says no iPod is connected even though when I plug it in iTunes connects automatically like I have requested. So. Thoughts?