You should hope for an AU where Peter gets his powers in grade school. .
Whether he's in high school or college, romance is gonna be a big part of his life.
To me, Marvel's just too repetitive in how they use it and too limited. They need to pick a lane and stick with it.
Have Jessica in a reoccurring guest appearance role(without the other Spiders) in Amazing Spider-Man, she'll quickly gain a huge following for readers. If Jessica and Peter work together (as often as he does with Black Cat) we might actually see a different side to Jessica that would be relatable with the readers... It's worked for Batwoman as a reoccurring guest in Batman.
Too many spiders kills the potential dialog between Peter and Jessica. Also, Miles, Spider-Gwen, and Silk share the same spider that bit Peter Parker. I want to see Spider-Characters who do not share the same origins as Parker become reoccurring guests, like Jessica Drew, Julia Carpenter, and Black Widow respectively.
Jessica has a lot of positive moments. She could fit in Peter's world very well. It depends on whose writing the character. I could see Jessica encountering Hammerhead, Tombstone, Mister Negative, The Jackal, and Morlun as part of her rogues. I could see Parker developing equipment for Jessica to enhance her venom blast...