In an interview with Collider, but coming to us via Eisner Award winning journalist George R. R. Marston at Newsarama, Marvel Studios head Kevin Feige had some big promises to make about the upcoming Spider-Man reboot. According to Feige, the new Spider-Man franchise could be like Harry Potter:
This is sophomore year, is the next one junior year? Is the next one senior year? Is there a summer break between each of those? I don't know what, but it was sort of how do we do a journey for Peter not dissimilar for what the students of Hogwarts would go through each of their years, which was one of the early ideas we had for the movies.
With roughly 2-3 years between sequels, that would put the now 20-year old "sophomore" Tom Holland at 38 years old by the time Spider-Man gets a Bachelors Degree, which would allow him to play his own grown-up self in the stage show "Spider-Man and the Cursed Child." It's also an ambitious plan for the franchise, which hasn't been able to survive more than three movies without a reboot, making it difficult for Spider-Man to ever complete high school. Still, it's good that Feige is looking to copy another franchise to make the third retread of Spider-Man unique.