iTunes woe

Aha! Next problem in my transition from PC to Mac is that my iPod is twinned with my PC and that's where I have made all my iTunes purchases. How do I get my music over from the PC to the MacBook without having to load the CDs one at a time on the Mac. And can I transfer the bought iTune tracks simply using the iPod as a sort of external drive? I rather suspect it's not that easy, otherwise the iPod would be the next great thing in illegal file sharing.

A quick Google search reveals a plethora of free or cheap utilities that claim to be able to transfer music to and from iTunes, iPods and iPhones. None seem very professional. I need to check out the support section of the Apple website first to see if they tell you how to do it - or at least explain what can be done.

Any Mac veterans out there know the best way to do this?