Guess nobody knows the answer to your question rob , i certainly don't as i know hee haw about anything Apple. You could try the...... Apple forums. If the answers not there try posting your query.
Hi there, Just a suggestion if you may... I use a program called media monkey for managing my iPod as I find I canot get on with apple software and the crap it installs. Using media monkey I have the option to transfer from ipod back to my computer using "move to folder" or "copy to folder" options then I can do the same when transfering items & playlist from hard drive to ipod. This way you can back up to your computer then transfer them back over to your iPod classic