If I were to reboot the MU...
I'd have Tony have been Iron Man for two full years, going on his third
Steve would have just been unfrozen.
The X-Men would've just come out onto the public scene.
The Fantastic Four wouldn't be public yet but they'd be there.
And Peter would've been Spider-Man for five months, now starting his Junior year.
I think, unlike other heroes, Peter is best spending most of his time as Spider-Man in school. I'd LOVE for every 100 issues to equal a year in every comic so to keep a standard timeline with the characters actually growing and thriving. The best way to do that is to return them to their roots for a bit or the place they work best. I think Peter works best in high school because he's iconic that way. If you spend enough time at the roots I think you'd have a solid way to move forward.
100 issues being a year? That'd put Peter in high school for around 200 issues. Then, he'd be in college for another 6 years, bringing that up to about 800 issues of Peter being who we want him to be. Once he's out, though, I'd love for Peter to become an Avenger, get a job at Horizon Labs and become a global hero. I'd say another year of that before commiting to a relationship with Mary Jane leading to the marriage in issue 1000. I'd say another 500 issues of marital growth before Peter's death with him survived by a kid and MJ. That's be cool.