Just wrote this in an email to a friend, so I thought I would repost it here… Apple intentionally doesn’t let you copy music from your iPod back to a computer – the best way is to go from straight from one computer to another (via a network, or perhaps you could burn some data-format DVDs, or perhaps you could get an external hard drive – which is good for backups too). That having been said, I did a google search for “transfer music from ipod to computer” and found some $19.99 “iPod Transfer” software (http://www.easyipodtransfer.com/showproduct.aspx). There is a free trial download that may be worth a shot.
I don’t suppose your friend has a Mac? (I would guess not based on your recommendation.) I use PodWorks to get music off my iPhone at work, and it works like a charm. Plus it’s only 8 bucks. http://www.scifihifi.com/podworks/