SoftMac, and all other Mac emulators, emulate the Motorola 68K series of chips. This limits these emulators to OS 8.1 or earlier, and applications that support the 68K processor. OS X, iTunes, etc, are all designed for the PowerPC processor, and in the case of OS X, it's a bit further, and requires a G3(PPC750) or higher. And don't expect a PPC emulator to come out any time soon. PPC chips have more registers than x86 chips; and when you're behind on registers, emulation is next to impossible(it can be done, but it's the digital equivilent of a root canal). Stick with something like Xpod if you want to transfer songs to an iPod, or get a Windows compatible iPod.