I get the feeling that it's the route they're going for with these films, which makes me so stoked.
I am assuming Vulture, Scorpion, and Hobgoblin will be involved.
Why Hobgoblin? He requires Norman Osborn to be the main villain for a film but it doesn't look like we'll see him any time soon since Marvel and Sony both said that they're interested in other villains for the time being and have little interested in the Green Goblin since he was part of the first two series. IMO, this is what's likely to happen with Sony's corner of the MCU.
2017
Spider-Man: Homecoming - Vulture and Shocker
2018
Venom - Carnage
2019
Silver and Black - not sure
Spider-Man 2 - Scorpion
That's confirmed.
Here's the speculation for the future.
2020
Mysterio's Menace - Silvermane
Kraven's Last Hunt - Lizard (and Spider-Man as antagonist in first five minutes and third act)
2021
Spider-Man: Ends of the Earth - Doctor Octopus and Spencer Smythe. (Peter Graduates High School)
Sinister Six in Spider Island: Spider-Queen (Black Cat and Silver Sable in 2nd Act, Spider-Man for last ten minutes of 3rd Act)
2022
Venom: Lethal Protector - Life Foundation Symbiotes
Sequel to Silver and Black
2023
Spider-Man: Invasion of the Spider-Slayers - Alistair Smythe. Norman Osborn briefly introduced along with his son Harry. Beginning of Phase 5 of MCU. Peter now attending ESU. Peter begins dating Gwen. Norman is the big bad of all of MCU Phase 5.
Spider-Woman - Brothers Grimm
(Can't see a sequel to Mysterio, Kraven or Sinister Six.)
2024
Spider-Man 2099 - Doc Ock 2099 as the villain
Venom Funeral Pyre - Pyre. Introduce Mania (Patricia or Andrea) as a sidekick.
2025
Spider-Man: The Goblin's Last Stand - Green Goblin. Gwen dies but Norman manages to get away with everything. Peter graduates college. Mostly setup for Avengers: Siege.
Silver and Black 3
2026
Spider-Woman 2 - Needle. Madame Web (Julia Carpenter) is a major supporting character.
Agent Venom - Crime Master. Flash Thompson becomes Venom.
2027
Spider-Man: Shadow of Evil's Past - Hobgoblin. Peter Parker is now a high school teacher in Queens. Miles Morales becomes his student/protege. It's mostly a mystery movie where we try to figure out who the Hobgoblin is but he gets away at the end and we see that it's Rod Kingsley after the credits. Ned dies. We see Donald Glover return Aaron Davis in the Prowler costume. We also meet the REAL Mary-Jane Watson. MCU Phase 6.
Anti-Venom: Nights of Vengeance - Stalkers. Eddie Brock gets an inverted version of the symbiote attached to him.
2028
Miles Morales Movie - Prowler. Assuming that Miles won't be known as Spider-Man in the comics at this point and will have his own codename which is why I'm saying, "Miles Morales Movie" instead of, "Ultimate Spider-Man."
2029
Spider-Man: The Wedding - Mister Negative. Peter and MJ tie the knot.
Venom: The Hunted - Xenophage. Eddie Brock gets the Venom symbiote back and is now having to deal with an alien who hunts symbiotes.
After this, do the Clone Saga where you still have Spider-Woman, Venom and Miles Morales doing their own thing but you also get Ben Reilly in his own spin-off series as Scarlet Spider which is intertwined with the Peter Parker films since by this point, most of the big stories have been adapted and Scarlet Spider is the only major spin-off series to not happen by this point. New villains would be Jackel (Miles Warren), Doctor Octopus (Caroline Trainer), Scorpia (Elaine Coll), Judas Traveller, Kaine, Spidercide, Scrier and eventually Norman Osborn returning. The series will be mature enough by this point that audiences can take a mystery unfolding over multiple films. The only other alternative is the supernatural stuff from the JMS run and I don't want Spider-Man going supernatural.