Only people at Apple in the iPod division know the answers to such questions. Seriously, what kind of answer did you expect to be able to get from the Straight Dope?
Not sure what you mean by this. iTunes sorts by whatever column you choose in any particular playlist. Are you sure you have the right column selected?
I doubt the regular iPod ever will due to issues of screen economy. I’d be surprised if the iPhone and iPod touch don’t already though.
I’m not talking about sorting in Itunes. I’m talking about the way the Ipod sorts in cover flow and album mode.
There are no screen economy problems. They already put some data (particularly with podcasts) behind a click of the center button. Older Ipods also allowed you to put the cover art behind such a click, saving the “play” screen for track data.