I have never used the Creative Zen before but he says it is way better than the ipod. The sottware was pretty easy to download and it did not give you all these pain in the ass options that itunes does to upload all your music files on to the program. It also does not restrict you to downloading music only from your PC to your ipod. With the Zen you can pretty much operate as you would with an external HDD.
It took about 15 minutes for me to upload 300 songs to the Zen. The Creative software however did not have an option to list the music out in order of the date it was added (itunes does) so sorting the music into a separate play list after it was uploaded took another 10 minutes. But the software does have other cool software to operate and manage your files on the Zen. In fact it was more interactive than the itunes I am used to.
I am still totally bummed though because I have loads of long ass train rides to go through next week not to mention a fucking long journey to East Africa that will take me through planes, trains, and automobiles. How can I do all that without my music? I had 1500 songs on my ipod that I loved. I know most people have thousands but I do not just upload songs blindly to my ipod, I chose each and every one myself. I feel like kicking Steve Jobs ass.