In reply to:

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On the insert sub-menu (Enque, Append, Replace) would anyone ever want these to Enque, Append, Replace shuffled?

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Yes, I actually use that functionality. For instance, if I've shuffled a whole bunch of tracks from artists X, Y, and Z, and I then decide, "hey, I'd like to get a few tracks from artist Q into this mix as well", I don't want to re-listen to tracks I've already listened to. Shuffling the tracks in makes sense in this case. It also basically makes sense from a UI standpoint, in that you've got shuffle selected as a global option, so it should apply globally.