One of the first complaints you'll hear from new iPod owners is that they can't (edit: automatically) sync their new toy with more than one computer or that they can't sync more than one iPod with one computer. Stop by any Genius Bar and you'll hear this common refrain.
Veteran iPod owners know that Apple limits the ways iPods transfer music in an attempt to placate the RIAA and keep the music labels happy so that they'll continue to hawk their artists on iTunes.
Apple's proprietary DRM software is called FairPlay and has drawn scrutiny of the EU as being anti-competitive. FairPlay is built into QuickTime and used by iPhone, iPod, iTunes, and iTunes Store. FairPlay protected song purchased from iTunes are digitally encrypted preventing them from being played on unauthorized computers.
TUAW has an excellent story today rounding up the software tools that allow you to circumvent Apple's FairPlay DRM on a Mac. Some of the local options include:
If you want to share iTunes over a network, your options include:
A new local software option called Misu (from the developers of Menuet and Art Collector) just entered a private beta period and allows you to connect two iPods to your Mac and sync them. If you hop over to TUAW you can get a code to test the private beta and if you email them feedback today, you'll get a free license to the software when it's released.