Finder stopped working correctly with my ipod classic, can't add music no more, what can I do?

I bought this Ipod fith generation that was working correctly before. I plugged it in, finder recognized it and I could use it to add music. Then I tried adding more songs with the automatically sync option and when I tried playing them they all skipped each other, none would play.

I was confused so I plugged it in again and did a "restore ipod" option. Since the restart (did around 3 of them) the finder menu won't no longer show me any options of adding music to my ipod. The Music app won't recognized that my ipod is in either.

Basically I don't know how to add music right now. As you can see in the screenshots the only options available in finder are either update or restart... I'm very confused.