Being a developer, who is constantly upgrading to the latest and greatest, on more than one occasion I have forgotten to de-authorize iTunes on the old machine before selling it.

A couple years ago I hit the 5 machine limit without realizing the importance of de-authorization. Apple support cleared my quota, and not so subtly let me know this was an exception, not a policy.

Why doesn’t Apple solve this issue for their customers and support staff?

Simply let authorized users/machines roll off after a set period of inactivity.

In other words, if a authorized user/machine has not accessed iTunes HQ for authorization after 12 to 18 months, simply delete the entry. If the machine attempts to access a FairPlay track, the authorization dialog would appear and a new period would be started.

This would go along way towards making the DRM used in iTunes more palatable, while reducing support issues and customer frustration.

Of course, you could just strip the DRM from purchased tracks, but that might make you a criminal or drug dealer, according to some.