"I understand what the OP means by shackled - as far as Apple are concerned you have to use iTunes"
I used to have another MP3 player and you had to use their management software too, so perhaps I'm just somewhat used to it.
Personally I find iTunes far easier to manage a large music collection with than just trying to do it through files. But then maybe that's the difference, I do have my entire music collection on my main iPod so it does need something that will look after it.
"it's still not a good example of either software architecture or design."
I can't see why...
Although I will admit that most of my iTunes time is done on a Mac and that I did try Safari on a Windows PC and thought it really rather rubbish and uninstalled it. Where as on a Mac it's my browser of choice.
In principle iTunes is a very good package that makes managing lots of music, much of which might have duplicate file names, very very easy. I realised how easy iTunes makes it when I started taking backups of my iPod to disk and started running into file and folder name clashes that iTunes does just take care of.
"As far as size goes, I don't store my whole music collection on my ipod, so I don't see this as a problem."
It depends very much on what you want your iPod for, and as said I've got both a Classic and a Touch as I can see very good reasons for wanting to work in different ways.
For someone like me who wants all their music on a gadget they can move around and doesn't want to faff about loading or unloading music from it trying to manage with an iPod Touch is a headache.
I don't want to have to think "oh, I'm going on holiday, I'm going to want X, Y and Z to listen to, right let's delete A, B and C and then load on the other stuff."
One day they'll release an iPod Touch with a much bigger storage capacity and I'll be content with just the one gadget :)