Yet to see a sensible explanation of how iTunes is so bad.
It's not so bad – but it's the fact that you have to use it, or other software to manage music files (sharepod is free and much better). itunes is more of a store with a player tacked on to it.
The iPod has 'proper drag-and-drop', in iTunes you just select manual management of music and video.
Contradiction in terms. With the Sony you don't need any software at all to transfer files.
Like a few others I have both a Sony and an ipod – Sony wins hands down for sound quality, although line-out volume is lower than the ipod. Sony UI is just as good as the ipod.
If you want huge storage, go for the ipod, if you want quality go for the Sony.