Hi
Mark.... - assume that you mean a 3G iPod Touch? If so, I have even the older 2G one which uses the old 30-pin dock to USB connector shown below - is that the one you are using also?
I've had this iPod for a half dozen years and have transferred well over a 100 hrs of MP3 music to the device from my MBPro using that cable and iTunes, so surprised that this connection does not work for you.
Of course, there are various ways to complete the process and I've always done a manual transfer (just don't like iTunes automatic syncs w/ music & photos - but that's me!) - I first put together a playlist (usually an album or more likely several combined for a couple hours of music) first, add the music, and then drag the playlist onto the plugged in iPod (see my screen capture below) - there I made a combo playlist w/ Kathy Mattea & James Taylor (it is located below what is seen), then simply drag & dropped on my iPod icon (blue arrow) - did fine.
So not sure how you are trying to transfer your music but if you do not have a LOT, this has worked for me over the years. My only other suggestions would be to 'Reset' the iPod (if not already done), and make sure the cable is otherwise working. Good luck - Dave
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