>>24798397 (OP)
I'm writing a more accessible fantasy retelling of the Divine Comedy (as a travel through a cursed "Dark Wood"), that tries to capture its main moral and philosophical insights in a more modern frame.
But then I realized that the story needs to be updated for modern times, to reflect what has happened in modern thought. So midway through, as the Pilgrim is finally starting to understand the true nature of sin, he is seduced into abandoning his Virgil by two figures that represent the twin lures of skepticism/intellectualism (based on Ivan Karamazov and Hamlet) and voluntarism (drawing on Milton's Satan of course). And so now I cannot just stick to a set model but have to figure out how the Pilgrim should get "lost in Hell" and how he might be able to find his way out.
I figured his crisis of faith should come at the "Gates of Dis" where Dante encounters the threat of Medusa, since this is symbolic of the need to "have faith (trust in what is higher in us) that we might understand" (Augustine/Anselm).
The problem is that this is requiring me to rework in a background where the Pilgrim has already been exposed to the ideas of mechanism and natura pura (and empiricism and nominalism) so that he can have something like modern doubts. I do not want these doubts to simply be overcome though, I want them to be sublated into a stronger understanding that transcends the immanent frame (I'm hoping that Sophiology, Mariology, and Solovyov's philosophy of history can help out here). And while I want to capture the insights of the Purgatorio and Paradiso (life as the proper ordering of loves) I want to end the story with the Pilgrim rejoining his Virgil to ascend towards purgation (expressed as the transfiguration of suffering).
But there is also a story within a story to help deliver the ideas where the Pilgrim reads a famous book based on Boethius' Consolation (only now Boethius is a sorcerer vizier). But I now think this needs to have a modern spin where the Pilgrim is given a different copy of the famous book with an alternate ending where Boethius takes a Nietzschean turn by conceiving of the divine as a sort of Calvinist inscrutable will.