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I had an idea for a Historical Self-Insert fiction:
I was reading historical SIs and wondered: how about an SI as Giuliano de Medici's bastard son, Giulio (Pope Clement VII in another life), reinvigorating Medici rule in Renaissance-era Florence and becoming best buds with Michelangelo and Machiavelli, with Da Vinci as their mentor. There could be a lot of intersections, including a lead-up to the unification of the Italian city-states under Medici rule, with possible influence on the discovery of the Americas.
Takes place after the failed coup against them (Pazzi conspiracy), right when Lorenzo the Magnificent adopts Giulio into the household.
What do you think?