To be clear again, Fiege don’t do over three solo movies.
We’ll get SM 2 this year and SM 3 in 2022 and that’s it.
Spider-Man will be the first exception to this rule if the deal is extended. Feige has referenced using Harry Potter as a template for the Spider-Man movies. With each movie covering a year of his school life. Its already been said that a potential third film would be Peter in his senior year at high school so a sequel trilogy would probably follow him through University and eventually getting a job at the Bugle or Oscorp. It would be really great if they play the long game with Osborn.
Here's how I would handle the remainder of Spider-Man in the MCU.
Spider-Man 3: Graduation (2021)- While dealing with his final year of high school. And figuring out his future. Peter has to deal with the uprising of Sinister Six. The end of the film would lead to their own spin-off under Sony. Venom is also teased. Octavius would make his MCU debut. We're introduced to Osborn, Harry and Gwen if this doesn't already happen in FFH. Osborn begins pulling strings in the background.
Spider-Man 4: New Beginning (2023) - Following his graduation from University, (yes there would be a time jump between the end of Gradution and New Beginning) Peter and MJ are engaged. Peter now has a full time role at the Daily Bugle. JJJ is finally introduced. Its been a pretty uneventful last couple of years until rumors start going around of a creature wondering the underground being described as a black mist. Peter quickly finds out that its the symbiote Venom. The film would also introduce Black Cat and Silver Sable. Setting up another spin-off for Sony. MJ would die at the end of the film after getting caught between the final battle with Venom. Setting up a relationship with Gwen.
Spider-Man 5: Hero Reborn (2025)
Its been a few years since Spider-Man's battle with Venom. Still carrying the scars of the fight and grieving the loss of MJ. Peter now in a new relationship with Gwen. Still blaming himself for MJ's death. And struggling to move on. No one has seen Spider-Man in months. Leaving the city vulnerable to new threats. In the rubble one of Spider-Man's most formidable foes kraven the hunter rises from the ashes. Miles would be introduced in the film. The film would setup a Kraven spin-off for Sony.
Spider-Man 6: Dark Reign (2027)
The end begins. Osborn makes his move. After years of planning, watching and waiting. The time has come to reveal himself to the world. Everything is on the line as Peter learns the truth about Osborn who has been responsible for everything that's gone on the last few years. creating the sinister six, Bringing the symbiote to earth. The green goblin rises. Peter faces his greatest battle. Featuring cameo's from the Avengers. A bunch of previous villain's would have cameo's. Peter would die at the end. Setting up Miles as the new Spider-Man.