I have paid my iMac 1500 ($1500) because I knew that, combined with my DSL connection, I could get plenty of quality freeware from Apple. This includes iTunes, in priority, but also Mail, TextEdit, AppleWorks etc.
All these applications have kept me from pirating Audion or Word, for instance.
The OS is expensive enough. The hardware is too. The Web services are too. If the software becomes $50/upgrade, I'll add a "Cracked Applications" folder to my Carracho server. Too bad for Apple.
But, as RacerX stated, I'm not really worried.