I watched From Russia with Love when I visited my parents and sister the other weekend, and since then have been doing a gradual rewatch of the entire official Bond film series. I'm also relistening to some of the audiobooks of the original Fleming novels.
I'm now ten films in and while they're less problematic than the books overall, my enjoyment of them has been tempered by the casual misogyny and even racism that I didn't see on previous viewings over five and in many cases over ten years ago. Anyone who one claims Sean Connery is the best Bond has answer to the fact that he's easily the most physically abusive, and that some of his liaisons (especially with Pussy Galore) don't seem entirely consensual.
From a technical standpoint, there were more obvious green-screen shots and day-for-night scenes then I had remembered, as well as more actual (and always female) nudity outside of the credit sequences. Reading through the film's respective casts on Wikipedia, it's also shocking how much voice dubbing there is too (e.g. British actor Robert Rietti does the voice of both the Italian villain Largo in Thunderball and the Japanese ally Tiger Tanaka in You Only Live Twice). Finally, the cliche of the villain expositing his plan to Bond when he ought to shoot him on the spot was also much more in evidence than I had remembered (here's looking at you, Goldfinger, Charles Gray's Blofeld, and Dr. Kananga).
All that said, I still enjoy the majority of the films I've rewatched thus so far. To me, the best has been On Her Majesty's Secret Service. Yes, I'm aware George Lazenby is no Connery, but that's no entirely a bad thing, and for a first film role, he did alright; I frankly can't see Connery's Bond ever actually being in love with a Bond girl, let alone enough to marry her. Possibly Dalton and definitely Craig, but not Moore or Brosnan.
The worst so far has been Diamonds Are Forever (The Man with the Golden Gun isn't far ahead, but is less dull and confusing and is elevated whenever Christopher Lee's on screen). Connery looks bored in many scenes and already looks too old to be Bond in most of them.
The ones that have gone down the most in my estimation are Thunderball and Live and Let Die. The former has too many underwater scenes (paging Chris Johnson and other classic film connoisseurs: Was underwater shooting a novel thing in movies in 1965?), though I also want to blame Kevin McClory (since it's fashionable to do so) for some of its pacing issues compared to previous films. Live and Let Die has some great scenes but the racial politics of the film (particularly with regards to the Kananga-Solitaire relationship) are hard to get past.
Outside of OHMSS, the one that's gone up the most in my estimation is The Spy Who Loved Me, which was more fun and less silly than I had remembered (though not without a few groan-worthy or icky moments).
Now onto Moonraker...