I am putting this putting this out on the internet so google will know about it and save other people some frustrations.
Generally, I like new versions of software. Amarok 1.4.4 and libgpod 4.0.0 break funtionallity, which is not good.
Problem: Files transfered to iPod will not play.
Solution: If you upgraded to the new amarok offered on kubuntu.org,
1) remove the deb entry from /etc/apt/sources.list
vim /etc/apt/sources.list
2) Update
sudo aptitude update
3) Remove offending packages
sudo aptitude remove amarok libgpod0
This should return you iPod to working order.