Which is why I don't have an iPhone anymore. iTunes is pure garbage. With my new phone I just plug it in, and drag/drop all the files I want. To and from.
I just generally stream cuz you discovery new stuff that way. You cant do that when you listen to the same playlists all the time.
Yeah. I agree.
Drag/drop ftw seriously.
Totally thinking about selling my iPod and buying an atleast 8GB + microSD slot Mp3 player.
My iPod barely has 7GB free (~1GB is the jailbroken OS, no idea why it's 1GB tho', need to reinstall stuff).
And now I have only ~400mb free (have some games, pictures on it too, which I to be honest never use/look at)
I only have 50GBs and around 11000 files. 
I think Naru has something already though. 
'Only 50GB' lol.
Well, somewhere I read that some have over 300GB of music, oh well.
Funny.