Thing is, I don't have an iPod or iTunes so I have no clue how that works. I imagine that it's not feasible.
To talk to the minty you have to talk over serial to the PIC. It has a USB port, but onboard this is wired to a USB to serial converter chip. So when plugged into the computer, the chip gets recognized and appears as a new serial COM port to the user, not a USB device.
Honestly, you're better off getting a flash card reader and popping the card out when you want to load more songs. The data has to go through the PIC when you upload over the USB/serial connection and the transfer rate is really slow, something like 4k/second.