Okay, let me start this story from the top. Spider-Man 3 was released to great commercial success and a degree of critical success, but the fact that the positive feedback wasn't good enough forced late production of Spider-Man 4. This, production issues and the fact that Sam Raimi wasn't confident he could make a film as good as Spider-Man and Spider-Man 2 in such short notice, caused him to abandon the fourth outing. This led to them declaring reboot, which I hate. The Amazing Spider-Man was released to average critical reviews and mild commercial success, but nothing was too negative (aside from me, of course). It was a solid start (according to some) and they went ahead with The Amazing Spider-Man 2 and halfway through, studio interference destroyed what could have been a decent flick. They announced The Sinister Six and Venom because they saw how successful The Avengers was and realized just how good X-Men: Days of Future Past would be. According to lead star Andrew Garfield, this is what may have caused the film to be less than good.
Now, unfortunately, Sony Pictures was hacked. We now have access to private information and while some people may be mad at their comments, please note, that is their private information, you and I are in no place to judge their opinions. We can, however, judge the facts. The second Amazing flick was less than amazing and it effectively dampened Sony's plans because Venom is cancelled, The Sinister Six is the main priority and The Amazing Spider-Man 3 is delayed. Out of all three of those films, the only one I would be excited in is The Sinister Six because it sounds pretty awesome based off of concept, but with The Suicide Squad taking off with Lex Luthor and the Joker, it now sounds pretty less than stellar. In any case, though, despite my feelings about the entire reboot situation, this whole plan, if initiated successfully could have been actually amazing.
Reports started off with the idea that Sony Pictures was considering a deal with Marvel Entertainment. This would have effectively rebooted Spider-Man once more, but the studios could not come to finalized deals over story, costume, marketing and creative control. It appears they had profits under control, but the entire creative process was the problem. So, even though these talks fell through, Sony Japan executives maintained belief that it could come through and apparently this was because, even though Sonyh hasn't officially fired Andrew Garfield, Sony Japan believes him gone and what Japan says, goes. So, with that said and in mind, Sony Japan believes that The Amazing universe needs to be rebooted one way or another. Sony, if they do go with this reboot in the MCU, want Captain America in The Sinister Six and Spider-Man in Captain America: Civil War. However, Sony's biggest gripe seems to be what film should they do next. At one point they were considering it being The Amazing Spider-Man 3 and then they changed it to The Sinister Six. Whether or not they reboot again is a moot point, the fact is, they don't know what to do next. Amy Pascal is reportedly going to have another meeting with Kevin Feige but the key thing to note is that if Avi Arad is involved, the whole thing is kaput. That's monumental because it would effectively push Avi Arad out of the Marvel Cinema business, and this is the guy who started the X-Men, Spider-Man and Fantastic Four film franchises and effectively started Feige on the path to the MCU. They had their split, but pushing him out, especially when he founded Marvel Studios, is tremendous.
Then comes in another variable: Jeff Robinov. This is the guy who ushered in such films like Batman Begins and Man of Steel but was also the man who claimed Superman Returns didn't gross enough (it did) and pioneered Green Lantern. He has left Warner Bros for Sony Pictures, and he did save WB and probably could save Sony as well. Amy Pascal is a good businesswoman who knows nothing about story, Robinov is a bad businessman who knows everything about story. In between their discussions came the possibility of returning to the Sam Raimi/Tobey Maguire pairing for another trilogy. It would work, definately, but Pascal is a proud woman. She shut this down claiming Raimi "Schumachered" the franchise, when that was actually because of her and Avi Arad not believing in Raimi enough. If he could come back, he could save the franchise, though. In response to that, Robinov suggested what I believe is a bloody brilliant idea. James Bond the whole thing. You have one set of films with Maguire, you have one set of films with Garfield, have a set of films with other actors and so forth. Given that Sony Pictures makes the James Bond movies, they probably know that this formula could work. Hell, it will work because it'll keep everything fresh, so long as they don't keep telling the origin story.
Out of all this, the one thing to note, though is that at this point, only one thing is for certain. In 2018, we will get The Amazing Spider-Man 3. As much as I don't like this series, it needs to end and have a conclusion. It's the best thing for Sony Pictures at this point, to end their current series. They could pursue placing him in the MCU after that, or they could reboot him once more. They could make spin offs in the Amazing universe while keeping the Spider-Man films on the backshelf for a while. Or they could do the smart thing and bring back Raimi and Maguire. All in all, though, all the discussions seem to point towards The Amazing Spider-Man 3 happening before any reboot or whatever will occur and these discussions point toward it being directed by Miller and Lord instead of Marc Webb. Chances are, if it does happen, and does get produced by the Russos, it will be the final non-MCU Spider-Man film. So there's the census: Spider-Man will get his third Amazing property as soon as Sony figures out what to do with it, and after that you may see him be like the WWE wrestler who was gone for long and join the MCU, or see Tobey Maguire come back.