Caravaggio was an epic troll. His Crucifixion of Saint Peter has a pair of beautifully lit buttocks in the left foreground, which (it is thought) are not accide

Caravaggio was an epic troll. His Crucifixion of Saint Peter has a pair of beautifully lit buttocks in the left foreground, which (it is thought) are not accidentally oriented towards the Carracci painting over the altar (Caravaggio's commission being for the less prestigious and remunerative side aisle). Whilst I do agree there was an element (a sizeable element: Caravaggio was an asshole) of "fuck you" in his choice of models, there's also a coherent philosophy or theology (and maybe even politics) at work. Consistently in his religious paintings he shows holiness breaking into the ordinary world, through ordinary and even reviled people. You see it in The Calling of Saint Matthew, where Matthew greets Jesus (who bears the merest hint of a missable halo) with a baffled expression and a "who me?" gesture. You see it in (the first version of) Saint Matthew and the Angel where the saint holds the book and the pen like an illiterate, and seems astonished at what the angel is guiding him to write. You see it in the Madonna of Loretto, where Mary and the Christ child are adored by a pair of instantly-recognizable pilgrims. (Pilgrims at the time, in Rome, were looked down upon and treated horribly, so depicting them in that scene was an implicit comment on their treatment.) This painting was also a magnificently petty troll, in that the pilgrims' bare, and very dirty, feet were directly visible above the officiant's head - it was originally an altar-piece - as he celebrated mass. It got moved to a side chapel soon after its unveiling. You see it in the Penitent Magdalen, which dispenses with supernatural trappings, and places the emphasis on Mary's interior state. (Some have noted the broken necklace as a possible reference to, and comment on, the violence that prostitutes often faced.) Coincidently (or not), the model for that painting, Anna Bianchini, was also the model (or the body, as it were) for the Death of the Virgin that you mention. Your gloss is excellent (and Caravaggio was certainly being provocative, and indeed perhaps validictory) but I think you miss one thing: the drapery. The top third of the canvas is taken up by a gorgeously-painted red cloth, the same colour as Mary's dress, which is an odd inclusion into this otherwise very realistic scene. It spreads across above the body, and then at the left is caught upwards, out of the frame, as though pulled by an invisible hand, or pushed by Mary's escaping soul. No one in the picture seems to notice, but it is in my opinion a vision of the Holy, as Caravaggio saw it, almost invisibly in operation just above, behind, and around the natural world.