The Mac Observer was able to spend some time with Bob "Dr. Mac" LeVitus and his review iPod unit this weekend, and together we looked at how to get around the limitations built into the iPod to keep users from sharing MP3s between different Macs.
Apple has officially said that one can not sync up an iPod to two different Macs. Specifically, Steve Jobs told the New York Times that music loaded up on an iPod can not be transferred to another Mac from that iPod. This has been an issue of some debate among Mac users, especially with those users who own and use more than one Mac (desktop and portable, home unit and a Mac at work, home unit and a Mac at school, etc.) who have legitimate Fair Use rights in transferring their MP3 files between Macs. As with all attempts at digital copy protection, Appleis measures are easily circumvented. This was noted by Steve Jobs himself as quoted in a San José Mercury News article by Jon Fortt:
There is some confusion about whether the iPod can be used to steal music. As the iPod is configured at the moment, the answer is absolutely yes. You can load songs from one Mac onto an iPod, and then dump those songs onto another Mac — or onto several other Macs.
Apple discourages music piracy. The company said it spent more than $50,000 on CDs to make that point at the iPod launch: Apple purchased and distributed 20 CDs to use with each iPod review unit, and iPods out of the box have a sticker reading "Do Not Steal Music."
Unlike some other technology makers and the major music labels though, Appleis position is that music piracy is a behavioral problem, and that it is futile to attempt to build encryption technology that forces people to change their behavior. People who are intent on stealing will steal.
"Every security scheme that is based on secrets eventually fails," Jobs said.
So Apple has made it a bit tricky to use the iPod to swap songs between two Macs — but only a bit. I did it by turning off the automatic synching feature on my home machine and dragged songs onto the iPod. I then connected the iPod to someone elseis iBook. That iBook already had iTunes 2 installed, and had already been linked to another iPod.
The iBook noted that this was not the usual iPod, and asked if I wanted to wipe all the songs off the iPod and start over. I said no. But the iBook recognized my iPod anyway, and let me drag songs off of the iPod and into the iBook.
In other words, by turning off the automatic sync functions and saying "no" when asked if you would like your iPod library erased, you can simply drag and drop your iPod music files from iTunes to another Mac.
Turn off the automatic sync setting
in your iPod preferences in iTunes 2