Originally Posted by
CuppyCake
If my OG ipod hadnt taken a shit on me..I wouldnt have this issue.
I had about 3,000 songs on that thing

You would stil have this problem because although there are ways to do it, ripping from your iPod to your computer is no fun task.
Burning all your music then re-encoding it to your computer is also another horrible way to transfer the music since Apple licenses it to a singular computer they make it a pain to migrate.