Is it possible to copy playlists and their included songs directly from an iPod to my PC?
Hello, you can read the following link. If you like what you read and it can help you achieve what you want, go for it. Of course there are many different paid and unpaid options out there.
Here is another tutorial about how to copy from ipod to pc, mac or linux for free:
For a free option software, you could try Sharepod. I think if you want to automate it a little bit more, this would be the best option for you.
Yes. iPod to PC transfer program can help. Thank you.