HELP! I can't transfer my songs!

So with my old original model dock connector ipod I was having this trouble where after my powerbook transfered like 300 songs or so, i'd get an error message saying "the device cannot be read or written to". A few days later, my ipod broke for good. I got my new ipod, and I'm now having the same problem. Someone else who was having this problem said to download the ipod updater, which I tried to do. However, it won't let me download it to my ipod because it says I must have Mac OS X 10.3.9 or higher. I have Mac OSX 10.3.9, but I tried downloading it again just in case. Nothing works. PLEASE HELP!

This may help try the trial version first
http://www.transfer-iphone-recovery.com/transfer-music-from-iphone-to-itunes.htm l

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