I feel this really comes down to the characters themselves. Certain characters only work one way, in comics or film. Superman, for instance, doesn't have a whole lot of flexibility when it comes to his interpretation, at least in terms of success to the fans AND the general public, which is what making movies on superheroes is about. So even though Donner's film is decades old, redoing it serves no real purpose, as any movie going forward will be depicting him in a similar way.
Spiderman I think falls into that category as well. Almost everytime they try something drastically different with him it doesn't work so good. If they decide to focus just on his school years without rehashing his origin all over again, it could still work. Possibly.
Batman on the other hand has had very successful interpretations that have been vastly different. As much as people may hate to admit it, goofy super-light Batman was a viable characterization at one time. Likewise if they want to make a film with him carrying a gun, at least technically, it would still be faithful to his earliest years. With Nolan, I think he's had success by taking the best of what works and using it to create his own thing. His own thing. In the future, I think it would be a mistake to try to duplicate what he's done unless he has some form of involvement.
However, I also feel that certain aspects have been nailed down to the point of overkill if it were to be retold. I don't think it matters what direction they want to go, his origin has been told in a very distinct way that would be almost impossible to improve on. Being a Hulk fan, even after two films, they still haven't completely nailed the character IMO, so in 10 or 25 years if they decide for another set of movies, they absolutely should redo everything, they still have the room to do that, to get it right. For Batman, Superman, Spidey & Ironman, that room has been taken away...