All right. Since you started this, I'll bite. ;)
The most 'auteur' : Skyfall. Agreed. Not the best Bond film, but certainly the most visually interesting (I love Roger Deakins cinematography and the visual journey from bright steely high tech to low tech dark fiery gothic).
The most 'spy' : From Russia With Love. Agreed.
The most personally consequential for Bond: OHMSS. Agreed. I didn't like No Time to Die and here's why: No Time to Die: A Broken Convention Too Far | Fanfare
The silliest : Die Another Day. Moonraker is silly, but that one somehow feels sillier to me.
The absolute worst: I'm tempted to go with Die Another Day (too silly even for Bond) but I'm going to go with No Time to Die for it's final unforgivable sin. It's certainly not The Man with the Golden Gun. That has Christopher Lee, dammit.
The most fun: You Only Live Twice. Completely ridiculous plot wise, but contains the best ever baddies base, Blofeld's face being seen for the first time, death by piranhas, tons of action, great pacing, amazing title song and music score, etc, etc.
The most cringe after childhood: Probably Moonraker. Too outlandish and spoofy.
The most disco: The Spy Who Loved Me.
The most Le Carre (in a bad way -- iykyk): Diamonds Are Forever.
The biggest disparity between theme song (high) and film's quality (low): I actually rather like Live and Let Die, so let's go with The Man with the Golden Gun (hilarious double entendre lyrics: "He has a powerful weapon...").
The most 'oopsie-we-made-an-ally-out-of-our-eventual-nemesis-in-real-life' : The Living Daylights. Agreed. I love The Living Daylights, but having Bond fight alongside the Taliban is quite the short-sighted faux pas.
The most nonsensical : Quantum of Solace (the script makes no sense, partly due to the writer's strike).
Most 'Bond Franchise' Film: Goldfinger. Yes, all right.
Most Iconic Connery: I'm going with Dr No, purely for "Bond. James Bond."
Most Iconic Lazenby : you get one choice.
Most Iconic Moore: Hmmm... Yes, The Spy Who Loved Me, I suppose.
Most Iconic Dalton: The Living Daylights. Agreed.
Most Iconic Brosnan: I'm not a huge fan of the Brosnan Bonds, but Goldeneye was the best of the bunch.
Most Iconic Craig: Skyfall. Yes, but I prefer Casino Royale.
Best Remake: How about A View to a Kill? It's basically Goldfinger with microchips. Yes, all right, Moore is too old by this point, but it's got Christopher Walken and Grace Jones, who are both fantastic villains. Plus I love the Duran Duran title track.