Change the model - Sell the software
If Apple really wants to make some bold economic moves, they should sell all the components of this digital hub (iCal, iTunes, Mail, iSync) and give service on top of it away for free. They could simply release new versions every year and charge for those versions. This gives people the option to choose what they want to pay for instead of being forced to just get it all or nothing.
People don't like paying for what was previously free - but don't seem to have any problems paying for software as is evident with Microsoft's office suite. If Apple took this approach, I think they'd be much better off in terms of adoption and profit.