Hate to say it, after hours of frustration with this "supposedly" simple program
I purchased Agile's Ipod converter (download demo first to see if it does what you need) and works flawlessly.
This is a result of a mfr rushing to market and assuming that all end users are engineers.
I do however love Roxio's main media creator program, in my opinion better than Nero's.
Even good mfr's make mistakes, this may be one to admit and shelf it.