This is exactly why i will soon be going back to linux/windows, and switching to android for my mobile device. For three reasons:
1) NOTHING is backward compatible in OSX; every time i upgrade to the newest OSX release, I conveniently have to purchase (again) the newest versions of my software.
2) I spend more time converting music files than i do actually listening to them, and yet still cannot add music from different machines. (This is obviously designed to force people to purchase music through the oh so convenient iTunes Store)
3) I shouldn't have to "break" my EULA in order to use my device to its full potential. Especially when there are open source products out there that do the same thing.
TL/DR: Once you throw down the comparatively massive investment and get an Apple device, you pretty much can only buy more Apple devices. Beautiful Hardware/Software, but designed to only function with itself, and poorly at that. This is why most IT people have always and will always prefer Linux and Windows. No hard feelings i still love you Apple, but i would only recommend your products to first time computer users, and the disabled. Maybe the future of Apple will be open.