Spider-Man 2017: Mysterio and A Human Background Figure(Osborn, Fisk, Silvermane, Hammerhead)-A personal emotional story deals with Peters psyci and the burden of being Spider-Man on such a young hero.
Sequel: Kraven(and maybe another villain like Chameleon)-expand on the tone of the first film and Peter trying to protect the ones he loves as well.
Third Film: Vulture and another villain(Shocker or Scorpion) so fans don't complain and b*** about Vulture being boring.-Make this a film less about punching and action and more about Peter using his brillaint mind for once.
Fourth:Venom and/or Carnage-It's been a long enough wait, have an movie focused completely and totally on Peter his relationship with Eddie Brock. Or Flash or whoever they make Venom.
(Also not sure which one of these films, but one should include a cameo from an Avenger or if the Netflix film bond is secured more freely, Daredevil.)
>If They Make It Beyond 4
-Five: Sinister 6-It's the obvious choice. This should be a defining and terrifying moment for Peter. Have him beaten to near death in the first fight with the 6. The go away for a while, the 6 go on a crime spree unstoppable for a bit. And
-Sixth Film: Goblin, this should be more than a long enough break for Goblin
This is where I'd end it off. Norman becomes Goblin finds out who Peter is, puts the ones he loves in danger. Then Peter beats Goblin somehow and continues on as Spider-Man.
By this time it should late 2020s to early 2030s. Holland should look like an adult Peter. End it there is what I say.