Free Sofware is future-proof and Apple products are not

"Free software", as in "free as in speech", means the freedom to run the program for any purpose. This means using my music software to play music in the format of my choice; it means owning my media in a format that doesn't lock me in to using one company's devices; it means knowing the program will still be useful if the original creator stops supporting it or changes it in harmful ways.

Avoiding the "Sorry, dad" scenario described in this article that describes, albeit from a different perspective, many of the reasons I've transitioned from a Mac geek to fairly anti-Apple (similar reasoning articulated very well by Mark Pilgrim) is a big reason savvy consumers of the future will (should!) consider open licensing an important criterion for purchase of any product.
Elgan says:

At least with Windows, you could reformat your PC and install Linux or any number of other PC-compatible operating systems. Can I reformat my iPod and install something else? Can I uninstall iTunes but keep using the iTunes store and my iPods? Apple strongly discourages all that, claiming that the iPod, the iPod software and iTunes are three components of the same product. But that’s what Microsoft said about Windows and IE.

Well, fortunately it's not that bad; my Apple-manufactured iBook and iPod didn't become useless to me when Apple's software stopped being worthwhile, because although Apple discourages the practice, they hadn't started actively trying to prevent users from installing the (free) software that would do what they wanted. Judging by the encrypted firmware that's preventing Rockbox from being available for the second-generation nano, they're starting now.

So yeah, the iPhone is sexy and tempting, but when I have the cash in hand for something like that I'm buying an OpenMoko phone instead. The iPhone would work great for a while, but just as I wanted my music player to play .ogg files and I wanted my operating system to give me greater control over the interface, I'd soon enough want my phone to do something it didn't already do; and at this point I'm not interested in supporting manufacturers who restrict my freedom to do what I want with the devices I've purchased.