Basing my thoughts off this:
http://www.ipodtouchfans.com/forums/showthread.php?t=755
But since iTunes is the only thing the iPoT wants to work with, could we play around with iTunes? Maybe make it so that it can handle importing irregular files onto the touch into certain directories.

that would be much harder and less convenient for hackers than jailbreaking it. Just imagine: we would need to wrestle apple after every iTunes or iPod update. More trouble than its worth. Of course, as the device is hacked, interfacing with iTunes would be very possible, provided we also find out how it communicates with the iPod.
By analysing and dissecting the firmware, we can gain an overall fuller understanding of how everything ticks. For example, it would be impossible to have created a custom devkit without the decryption of the firmware.

Ok oh well.