In a recent podcast, a guy complained (damn non-internally-permalinkable things — fix that!) that a big problem with the iTMS is that the files are locked to a given computer and that, if that computer takes a dump, you’re screwed. He complained that Apple makes it too hard to back your songs up.
For all the complaints one might have about Apple selling DRM’ed music (and I have some myself), the idea that the songs are “too hard” to backup isn’t a valid one, IMO, since all the tools necessary to do the backups are built into the application, and they’re not hidden, either.
Really, there are only 2 steps to backing up your music —
Creating a smart playlist
You now have an ISO-formatted CD or DVD that you can place in a media safe, a safe-deposit box, mailed to your nephew, or whatever. None of this is hard.
The Celts invented two things, Whiskey and self-destruction.