Okay so here is the deal: I have an iPod classic 160 gb and I am using OSx 10.6.8. I have my music stored separately on an external drive because there is too much for my computer. Recently my iPod started not syncing up properly. I don't sync all my music so the iPod isn't full, but it had error where some songs would randomly turn into other songs by completely different artists. Other times it would go silent and then skip the song entirely. Sometimes only a few seconds would play and then it would skip. I decided to restore my iPod and re sync entirely. When I went to do so, the iPod connected perfectly fine. After the restore, the ipod wouldn't connect for fifteen minutes. I tried treating it as a disk and erasing and repairing it, but that didn't help the problem. I went and restored the iPod again, making sure to clear crash logs, but it didn't fix anything. When I finally did get it to sync it took about ten minutes a song. This has never happened before even on my first sync. I had my music on an external hard drive then so I don't think that's the problem. Can anyone help me out with this?