WARNING: Long Post (Summary in comment)
Without any delay, straight to point, ofcourse you have to remember or rewatch the movies if YOU want to be sure. I won't try to establish a timeline but just lay it out there.😁
First, who is said popularly(but never ever officially, specially not with current meaning)a Re-boot.
Craig Era:
FIRST It starts with a B&W scene, usually used to show past, the trailer teasers were advertised that way, 'past of your hero', it shows the actions that led to him gettin Double O status. Then it cuts/jump to colored scenes, LeChiffre the villain with blood tears and parkour scene where 007 is experienced enough to get annoyed by a rookie touching his ears.
Then after getting out of hospital, there is some time spend with Vesper, then after the line "the bitch is dead" and James checking the phone, we see Mr White getting shot in leg. WHICH opens up and continue in QOS opening titles, he is escaping gunfire car chase while kidnapping mr white. The movie takes place in 2008, which is atleast 1 year gap, So? there is again a timejump.
QOS, pre-title is very close to its main movie and ending. THEN
SECOND Skyfall 2012, takes place definatly after quite some time. It uses past/legacy and depends on it very hard. That is, to believe in the movie one have to know and have familiarity with character, as he is now a 'Old Dog'. We will cut of 'just nods/winks/homages' becasue there is limit to them, you have a object/car which is running and firing around becomes vital part of movie-in-universe. SO, whats there, Aston Martin with same number plate, M. knowing about the ejector seat(M, Q, Moneypenny have always been treated as regulars/stand-ins).
No its not the same car from Casino, THEN, Goldfinger, Thunderball have happened, there was a previous Q, old too, because 007 was surprised to see a young person and he says 'not exactly christmas', so he is used to high-gadgets. Without it all feels illegitimate, a movie have to have in-universe explaination, like Goldeneye opening scene of Aston drive, because they never deny it same guy.(They were trying to get same number plate in 1995 but legal problems).
Current-Time/Events were always just setting where the movies took place to tell the story.
So, craig's Bond have gone to Goldeneye, Thunderball, Goldeneye somehow-someway. As we see NTTD, we then know that he have even have The Living Daylights adventure.
If you notice, after Sam Mendes, there is so much emphasis on 'the world has changed, old ways etc.'. It all feels out of nowhere and without weight, if its not somehow, someway connected to previous movies.
OKAY, I won't enforce anything, I just put it out there what I saw as factual. That is they might have.
Connery Era:
What was the connection between Dr No and Russia With Love? A hidden organization's revenge. They were still more or less free. Goldfinger was completly free. Even Thunderball is standalone aside from the villain working. Bond is fighting them just from his side without much knowing about 'Spectre/Blofeld'. Until You Only Live Twice. Where he meets Blofeld for first time. You can't be sure how much time passes between each film.
Then, Lazenby Era On Her Majesty's Secret Service have another actor play the character, they thought that having their biggest villain yet is the best idea, and writers decided to lean on the book, making him meet here for first time, 'again'. So ONE/fan must overlook it, for his interests sake while making it as contextual as possible. Maybe one can RETCON and see that either he didn't see him face to face in YOLT or that YOLT takes place after OHMSS, and he meets again, but I will go with the previous option.
Next, Diamonds Are Forever, Bond is very eager to find Blofeld in the pre-title sequence. More angry and hard hitting. Ofcourse he can't kill someone out of personal vendetta. He in the end(of pre-title sequence of DAF) 'kills' Blofeld, his anger cools down and he moves on. Some time have probably past between that and main movie. Where Blofeld once more? make a absurd plan/revenge/ escape?-probably as he returns in FYEO. We will get to that.
Moore Era:
So, it starts with Live And Let Die, Bond is an expert and experienced agent here, as he seems to be at more ease and less taking things personally(not that he don't have personal feelings involved).
The Man With The Golden Gun, The Spy Who Loved Me, Moonraker, then For Your Eyes Only, here Bond have become experienced, and have made admirors/adversaries(Scarmanga etc.)
In FYEO, pre-title sequence we see, him standing infront of Tracy's grave, that prooves that event of OHMSS, somewhere. THEN octopussy, never say never again, a view to a kill, living daylights. (I will tell about NSNA and TLD later).
Dalton Era:
In Living Daylights, Bond feels more youthfull, doesn't he? then in Licence To Kill he is more mature, ofcourse he never a rookie. But definatly that. So in LTK its mentioned that he was infact married 'but that was long ago'. THEN
Brosnan Era:
Goldeneye film starts with pre-title sequence which takes place 9 YEARS before actual movie, where he iss accused of being a 'relic of certain war'. A dinasour. So that equal to being over-expert. Lot of experience.
There is no factual detial of when the next movies take place and how much gap is between each of them. I personally don't find him old or that-old looking in either Tomorrow Never Dies and The World Is Not Enough until Die Another Day. If I remeber correctl he have little white hairs. There is ofcourse him being in korean prision torture. 14 months.
Other thing, Bond was re-evaluated in 1995 movie, while he was taken a job as trainer or retired and then called back and re-trained in Never Say Never Again, I know non-eon. but Fatima Blush😍
SO THAT IS THAT.
Now, you can see many timejumps and undefined gaps between movies, or in movies themselves. Again, if ONE chooses or get interested in making a as valid and profitable to ONE's personal desires of/from James Bond 007 movie franchise, he or she may, in this case like me see and choose:
[Spectre 2015, NttD 2021 are complete blunders, some of Skyfall too(like not saving Severine, making Moneypenny field agent, idiot of a Q, M dying), even QOS which I love, some part of it too(like not well executed and written,i.e. not bringing back formula and still whining about vesper.), OR any part of the movie which contridict what you want or probable continuity, can be cleared in portions, like he won't completly meet Blofeld in YOLT.]
This all could be cleared in as part of Fever Dream that Bond suffers in Die Another Day torture sequence, even that movie itself is seemingly 'over-the-top' becasue of Bond's unhealthy state.
OKAY, I would do this that is remove 2015 and 2021 movies almost completly and etc. than loose my liking of 'same old james bond'. That is I will treat CR2006 and QOS kind of prequels. LALD taking place between them as it was next novel after casino, along with TND, as it have have new kind of villain. Dr No is the first mission after 'that black and white scene and getting double o'.
TLD(youth feel) can take place after DN, same goes for FRWL, as it is immidiate spectre's revenge.
after quantum, movies like from Goldfinger, Goldeneye's Arkangel, Thunderball, YOLT, OHMSS, etc. could take place.
From TMWTGG, TSWLM, MR, FYEO(after OHMSS), TWINE, GE, AVTAK, LTK(after FYEO). SF(severine is saved, M don't die, just retires, q is not idiot, moneypenny is just desk worker).
Octopussy(Bond have been working long enough, that a 'victim' of his, daughter has became a danger),
NSNA after sometime.
There is lot of space where next james bond movie(s) could take place, they just have to follow the formula, make standalone-episodic, balance of campy and gritty. In first movie they can make joke about Moneypenny killing Bond, nightmare of having child and replaced, few refrences to past films, like dusty files of {skyfall, arkangel, dr no, moonraker, scanchez, thunderball etc.} and move on, with next movies simply being normal james bond movies.
END
Its fun to imagine its same Bond fighting and going through adventures of moonraker, living daylights, dr no, you only live twice, thunderball, live and let die, octopussy, the world is not enough, skyfall, quantum etc. Its a reason I like him, a kind of unsaid immortal feel, a forever friend. Different times and places.
Ofcourse one must know and accept that not one single James Bond movie actually follow any timeline/storyline/continuity, NO not even skyfall, quantum of solace, spectre, nttd, No not at all. Its just a FACT. Same goes for each actors.
One must take them as stories, and if interest there make a storyline by himself.
The logo and titile is by me for a james bond movie. FAREWELL, it will be my last post. for a long time atleast on bond or on reddit.