1.) It's not like I was wandering through the root playlist, heard a song off of Mindcrime and said "Hey, that's what I'll listen to"... it was one of those, "get in the car and decide.. hey I want to listen to Mindcrime".

3.) Encoding as a single MP3 prevents single-songs from the album from being thrown into the random mix.

Oh, sorry, I've got a bit confused as to what you're asking for here. If you want sometimes to play everything at random (with Mindcrime tracks shuffled in), and other times to listen just to Mindcrime all through in the right order, that's easy. Mark the root playlist "Always randomise", don't mark the Mindcrime playlist "Always randomise".

That way, choosing to play the root playlist will get you everything at random (including scattered Mindcrime tracks), and navigating the menu to the Mindcrime playlist and playing it will get it all in the right order.

Peter