An interesting scenario. I especially liked the episodes you’d chosen as the "four times". Harry’s initial lack of concern seemed quite believable, given the circumstances, and the ease with which Severus was able to sweet-talk him into doing what he wanted made me wish Harry’d remained oblivious. *shudders*
I’d love to know what were the challenges of being a Muggleborn in the Wizarding World Hermione referred to; it’s hard to believe an adult, well-informed Hermione would buy into some nonsensical "evil Purebloods" propaganda just like that or happily marry the Chihuahua-fondling Finch-Fletchley.