Hello,
When you connect the ipod to it, does Windows recognize or alert you that something is plugged in?
While you're at that:
When you're on iTunes, click the square on the left with a little arrow pointing down. It should bring up a drop-down. Click "show menu bar". Once you have, it should show a menu bar right below the play, back, and forward controls. Click "help", at which point it should bring up another drop down. Then, click "run diagnostics".
It will bring up a window. Uncheck all the boxes except "device connectivity test". Click next and let me know what it tells you.