Impossible, you say. Piffle! Not for Rogue Amoeba (that one celled organism is a determined little guy). They looked at the problem and thought of LiveDisc. LiveDisc is an application that is burnt onto the CD. This application points to the most recent versions of the actual app that you want the user to install (an Internet connection is required). A simple solution to a highly specific problem, which is why I like it so much.
Rogue Amoeba is now sharing LiveDisc with other devs in the form of LiveDiscKit, an open source plugin for Interface Builder. Simply tweak a few settings, point it at the right places, and you're set to press a large number of CDs which will never go out of date (CD pressing functionality is not included with LiveDiscKit), that is assuming CDs stick around for much longer.