2 iPods + 2 iTunes - iServe = frustration

I have defended Apple's FairPlay DRM in the past, partly because it appears to emphasize fair use, allowing multiple burns of a playlist to CD, and letting you share your music to 5 computers across the network, and an "unlimited number of iPods."

My perspective has changed a bit. Christy's iPod mini, ordered in late April, well in advance of her birthday and Mother's Day, finally arrived in time for back to school.

So here's the setup: I have my PowerBook, with much of our CD library and all the iTunes Music Store purchased music. Christy has an iMac with a different set of tracks from our CD library and no iTMS songs. Christy has a 4-gig iPod mini, and I have a 1st-generation 5-gig iPod.

Here's what I expected: I thought that by virtue of having FairPlay-authorized iPods attached to FairPlay-authorized computers, iTunes would manage things, and Christy and I would be able to shuttle music from either computer to either iPod.

That is, in fact, NOT the case. Given Apple's provided software, the iPod can't pull music across the network, and you can't set up an iPod to pull 3 playlists from computer A, then hook it up to pull 2 more playlists from computer B. If I want to put purchased songs on Christy's mini, I have to populate it only with songs from my PowerBook.

Apparently, Apple assumes that every family will have a central computer that holds all your music, and every iPod user will go to it to sync their iPod. Hasn't Apple heard that people carry these “laptop” thingies nowadays? I don't want to leave my purchased tracks at home when I go out of town, although I suppose I could bear it if they're all on the iPod. The only way I could see the central computer approach working is if Apple shipped an iServe, with built-in iTunes synchronization (not just Rendezvous, er, OpenTalk sharing, but full synchronization).

One solution I may actually try is to cross-synch our iPods, with Christy's iPod featuring songs that are on both computers and songs that are only on my computer, and my iPod featuring songs common to both computers and songs that are only on her computer. That way, between the computer and the iPod, we would each have nearly a full set. Still hardly an ideal solution.

The longer-term solution is likely one of the million iPod manager programs out there, so I guess I'll start messing around with them, and I guess I'll have to check out Hymn and DeDRMS. It just seems really bizarre that I've bought into Apple's system from end to end, but it doesn't work like it should. I welcome correction, if I've overlooked some setting or shortcut, and I welcome pointers to any of the iTunes/iPod tools that people have used in a similar situation. This strikes me as profoundly contrary to true Apple-ness, and to the ideal of "personal" computers.

Update 8/7: This is actually easy, but completely separate from iTunes itself. Apple has a useful how-to, and it's as simple as copying the files over to a computer that's already authorized. My mistake was expecting it to all work from within iTunes.