If that's the case, then there's also a bit of a UI issue. The current shuffle button is a toggle, not a "click once each time you want to shuffle" button.
Yes, for sure. My speculation (from vague recollections of ancient Slashdot posts I didn't read closely at the time - never having used iAnything for music myself - so take it with a grain of salt) is that shuffle started out randomly picking the next song, but people complained that IT WASN'T RANDOM because they kept hearing the same songs - but of course if it is random, there's no protection against precisely that, and the people for whom it has happened to be well distributed probably arent' going online searching for "itunes shuffle randomness problem" or whatnot. So there may or may not have been a bug in the randomness, but randomness isn't really what people wanted anyway, and upon realizing that they changed it to the way it works now - where you shuffle it like a deck of cards, and then run through that deck repeatedly. Now, shuffle is an action where before it was a mode - and they forgot to change the UI to match.
For a playlist, it's "sort by the original arbitrary order that the user put it in" so you can't rely on the usual sort methods - e.g. clicking the column header.
