I found that fully uninstalling iTunes fixed the problem. Some part must have been hanging around mucking up the transfer.

I have been trying out MediaMonkey and was transfering audio book files to my iPod and found that the files do not end up in the order that I put them in before sync'ing. I looked through the settings and did not see anything about sorting, did I miss something.

iTunes does put them in order but is a pain to use. MediaMonkey has a well done interface, and I would like to use it instead.

Thanks...