Hi Simon, I suspect there could be something wrong with your iTunes settings file. You don't write if you are on a Mac or Windows machine. Try to do this:
- Quit iTunes and disconnect your iPod
- Move out your iTunes folder to the desktop (do not delete it! We will need to put it back afterwards). On Mac OS X it is default here: ~/Music/iTunes/ and on Windows here: \username\Music\iTunes . Remember the location you found it in.
- Start up iTunes and you will be prompted the questions like it was the first time itunes was started.
- Your iTunes will be empty so import som music into it for testing. Insert your iPod and sync it from your new iTunes setup.
Test to see if this helps to play more than 3-6 songs. If it does then you need to rebuild your iTunes catalog. Let us know how this works first. If you need to you can now quit iTunes and pu back the iTunes folder from your desktop. Then your iTunes setup will be like before the test.
But let us know who this first test works!