Re: Tranferring music from iPod to iTunes
I have tried to use the drag and drop method and it does not work. It has already been connected to my computer so it won't sync
Using ALL Apple hardware should be easy for it to sync and as told by Just_Me there should not be a reason why it won't sync.
A few things from my own experience with a Gen 5 device, If I did not use a USB connection from the side of my MacBook as opposed to a USB Hub powered or not it would not work.
Also you can burn the CD and wipe the iPod clean, update any software it detects, resync everything after you put the CD you burned and rip it into iTunes. That should work ( Don't forget you have to create a playlist to burn the CD w/i iTunes.
The only reason I mentioned the Gen 5 is because I don't know what you have and it was a bit finnicky. My Gen 7 works perfect now with no issues.