I have tried to use the iPod as a Hard Drive many time before, for files transfers as small as 100MB. But, with the latest Mac OS software and the latest iPod OS installed at the time (this being the days of 10.1.5 up through 10.2.3) I had countless -36 errors, interrupting my file transfers, and causing the I/O processes to be halted for over a minute before I got the error message.
(iPod: 5GB model)
This even occured multiple times after I refreshed my computer and iPod completely and installed the latest software. I have had no success to navigate around the situation except for not using the iPod as a Hard Drive.