This is a good question
ROL would be the most consistent in terms of wall to wall brilliance, but we’ve practically had this on the DWT. Also it’s very specific musically and might get a bit one note for a concert.
LAP would have the highest highs but some of it would drag.
I’d personally love BS but it’s too obscure and the atmosphere wouldn’t be the best
True Blue is the closest to a greatest hits concert, but it’s way short and personally I don’t care for 2 of the 3 singles as much as everyone else.
Erotica would be the best concert IMO. You could do so much with that variety of sounds while still having a running theme that you get could quite creative with. Then again, who wants to see her recreating this at 65.
Confessions hasn’t aged well for me. It would probably be received well but it only contains 1 truly iconic song from her catalogue
I’ll go with True Blue.