Heya *!
Wow if you guys are going to throw the hate, please make sure you aim it in the right direction…
I own the iPod, music on it and the computer???
No you own the iPod and the computer, but according to the various recording industry associations, you are only renting the music…and they would prefer that you buy re-rent it for every new format it’s released on, and also buy rent a copy for every device you might possibly play it on.
The rules about how/what you can copy from one device to another are set by these media cartels, not Apple, not Microsoft. We are talking about groups of lawyered-up profiteers armed with a majority of the money you have ever spent on music, whipping a dead business model for all they can get out of it. You will find the same if not much worse DRM issues with any media device that has been blessed by the rights holders.
Ever tried to “squirt” (their word not mine!) a hit song from Sony or Universal on a Zune back when they still had that feature?
Where I live they have bought so much legislation that my tax dollars are being used to prosecute file sharers in criminal court, while just about every other industry has to handle copyright infringement problems in civil court and on their own dime (as it should be).
It’s easy to bash y if you are a x owner and vice-versa, but there are other forums on the net dedicated to that. 
if software company’s can cash in on on this why cant we have this as a part of the package?
Considering how many free options there are on the mac side to do this, I have to wonder if there are also free tools for Vista that simply have worse search engine rank than the crippleware anklebiters.
The last time I had a look at the process, for itunes store bought tracks (or anything DRM locked to your itunes account) you simply chose “Authorize Computer” from the itunes menu and every track bought from that account can be pulled for free to the new machine.
Then for the DRM free and non-store tracks (or tracks you want to convert to DRM free) give Songbird a try. It’s free (mozilla project) and cross platform. It is dressed like a media player/file manager, but it also has two way itunes library import and export. Run it on the old machine, import itunes library into songbird, transfer the songbird library to the new laptop, and export it to the new machine’s itunes library (if you are staying with itunes). No need to fight with an ipod when all you need is a lan connection or usb key/sneaker net. 
Another thing to consider to avoid future DRM mess is alternative firmware for your player…Rockbox and some other free firmware packages put the controls back in your hands.
Back to the kit mill with me!
Best regards
SmashTV