iTunes is the biggest problem with the iPod over most other MP3 players.
Because of the need for that software, and the whole AAC file format, I have been severely put off by it.
Most other players act as a hard drive, and allow you to just drag and drop like you would do with any other drive.
This also makes it easier for you to transfer to someone elses PC, as my understanding of the iPod is that once its on your iPod, a file cannot be transferred back to a PC, and certainly not in MP3 format. (is this the case?)
Granted, my MP3 is very bulky, which is something the iPod has it beaten on, but thats because I wanted an MP4 player as well, with a decent sized screen.