I heard an interview with Tom DeFalco this summer where he explained that after he and Ron Frenz were removed from Amazing Spider-Man, they were putting together a pitch to take over Daredevil, but editor Ralph Macchio needed a new team on Thor so asked the pair to take over that book instead. I loved the Nocenti/JRJR run on DD, but I spent a while trying to imagine what a DeFalco/Frenz DD run would have been like. Which lead me to start swapping creative teams from various eras around.
Ann Nocenti did the Mad Dog Ward stories, the first two Web annuals and she did a great one-shot with Rick Leonardi of Spider-Man vs. Thanos. Imagine DeFalco and Frenz taking over Daredevil and having her and Leonardi or JR JR do a run on one of the Spidey satellite books at that time instead. When Conway was doing both Web & Spec, there really wasn't any tonal difference in those books (they were really almost like a bi-weekly book with two different artists) so it would have been interesting giving one of those to Nocenti to do some of her darker, quirky Spidey stories.
Going back to the 70s, I'm bummed that we never got a Steve Gerber Spider-Man run. It was a character that seems like it would have fit in with Gerber's sensibililtes pretty well. It would have been cool to see him paired up with Gene Colan on early Spectacular.
In the 90s, Fabian Nicieza and Darick Robertson could have done a really fun book based on their work on New Warriors. Brian K. Vaughn & Adrian Alphona could have done some interesting things with the book after they wrapped up their work on Runaways.And Matt Fraction would have done a real quirky run, possibly working with some of his artistic collaborators, like the Dodson, or Jamie McKelvie.
This isn't meant to slag off on any of the folks who actually did the Spider-man titles at the time, just a fun thought experiment about what could have been if things had gone differentlly.