The "One Bad Day" line of Batman one-shots has an excellent concept. Top tier talent tell self-contained stories in which major Batman villains go further than before, with the idea of doing for those guys what the Killing Joke did for Joker. So Tom King and Mitch Gerauds did a Riddler special. John Ridley, an Oscar-winning screenwriter, teamed up with Giusepe Camuncoli to do a Penguin story.
Is something like this feasible with Spider-Man?
It seems to me there are a few knocks against it.
A big part of Spider-Man's appeal is that things change for the character issue by issue, so his most acclaimed stories are typically part of larger runs. The main exception would be Kraven's Last Hunt, although that creative team had previously worked on the character, and DeMatteis would return for three later runs and assorted other projects.
"One Bad Day" is a vehicle for popular talent to return for one story, but we've got that in the Spider-Man comics, with Zeb Wells & John Romita Jr on Amazing Spider-Man, Dan Slott & Mark Bagley on Spider-Man, and Joe Kelly on mini-series and a fill-in arc of Amazing Spider-Man.
There's a precedent for a series of Batman one-shots based on an acclaimed story. It doesn't work as easily with Spidey. A "Fearful Symmetry" line of TPB-length stories might be too much content. A "Nothing Can Stop..." line of books adds up pretty quickly. You can't really have a line of one-shots based on "The Night Gwen Stacy Died" with supporting cast members getting murdered.
But I've figured out a way it could work, which I'll share a little bit later.