And, as a side note, is there any software more universally frustrating to work with than iTunes? That was my biggest reason to research Android phones as opposed to just getting an iPhone myself, and I'm glad I did. I wouldn't want to fight with iTunes to figure out how to get albums onto my phone.
I have heard this quite often and never experienced it. I have an android phone and I have literally purchased music that I already own and is part of my iTunes library just because I didn't want to bother picking through folders to drag and drop music onto it.
If you set up iTunes correctly it is far better than anything I've experienced with android. Plug your device in, check a couple of boxes to indicate anything outside of your smart playlists that you might want to add, click sync. Done. It's even easier with my iPad since they've implemented wifi sync on ios 5, which I assume is also true for iPhones that support iOS 5. I've never had any trouble at all putting exactly what music or videos I want on my iPods and iPad, yet I've had the same music on my android phone for months simply because I don't feel like mucking about in the file system.
It mystifies me that anyone complains about iTunes being frustrating. It has worked far better for me in putting exactly what I want on the devices I have that support it than anything else I've tried. The only thing I've tried that even approaches it is Winamp, and I'm pretty sure you can use Winamp with iDevices too. But why would you want to use something that is just like iTunes but not as intuitive when you could use iTunes?