Forgive my long answer, but you have quite a few good questions and observations.
I'm curious, how many of those who prefer Moore over Connery (or any of the Bonds) got their start with Moore?
Whomever we grew up with matters a lot. And I grew up with Moore (although my very first was with Connery), so I would be a fool not to accept this as part of my favouritism. The general consensus seems to pedestal Connery, and I do not think it is completely fair. Stop most none-fans in the street and ask them, and I will bet you they will either say the latest Bond (whomever he may be) or Connery. Stop most diehard fans in the street at I bet you most of them will say Connery or Moore... and a few will mention Dalton.
Of course Connery is great and he did after all help establish the personification we love to day. He was different, he was tough and he connected with male and female audience alike. Without him, perhaps no franchise and thus a completely different take on action movies in general in this day. I salute him for his part in cinema history. However, if scrutinized only three, perhaps four, of his seven Bonds films are imo still good.
When I wrote my OP I had just watched them all over a relatively short period of time and so I had a fresh perspective. I expected to favourites them both, but what surprised me is how wonderful I found Rogers version to be - even when meddled amongst fantastical elements like in Moonraker, his Bond came off solid and intense.
I find it hard to fathom that anyone who got their start with Connery, especially Dr No or From Russia With Love could ever think Moore surpassed those roles.
Indeed, it is very much a religion and to me too I guess. And I agree, those two are in the very top (in my top three for sure). But Connery was in more than just these two pearls and should be judged more broadly.
In the books, Bond is often described as cruel and cold, something that Moore never, in my opinion, projected on the screen.
Connery has this wonderful moment in "Dr No" where his ruthlessness shines through everything and you realise he is a force to be reckoned with. It is when he executes a guy in his bedroom the very second he got his needed info. A moment like this is far in between although imo Roger has quite a few of those, and if we put them back to back I think more than Connery. E.g. in the iconic Goldfinger Connerys most tough moment is a forced role in the hay.
To me, Roger Moore is ruthless in just the right amount, and you can hint madness behind his eyes from time to time. The more cheesy remarks are often in times of hard distress and so, in a way, makes him seem even more cold and calculated.
In his first installment he outright cheats a poor virgin to have sex with him. In "The Spy Who Love Me" he knocks a guy down off a roof the moment he get his info – not unlike how Connery did it in Dr No – but Moore does so a split second
before he got the info; very cold. I don't remember seeing Bond this cold in any of them since... beautifully played. In "The Golden Gun" he has a fight with three men, where he beats one of them by hitting his head three times in to the wall – where one is clearly enough. This fight rivals the great train fight in From Russia with Love. Another of the finer moments is when Roger kicked Locque off of the cliff in "For Your Eyes Only"; also one of the coldest ever filmed in the Bond universe. The way he just stands there and looks at him when he does it. Another moment is when he threatened Rosie at gunpoint AFTER they had sex in "Live and Let Die" and with complete suave coolness says, "Make your choice?". "In A View To A Kill" he plays a playboy as part of his undercover and this undercover was done to animated for my taste. But upon rewatch and when he is himself in the frames (and not his undercover silly persona) he is unusual cold and his hatred towards Christopher Walkens character is intense....
In a fictional matchup, I think Connery's Bond would wipe the floor with Moore's Bond, although Moore would probably have some better bon mots!
.... they would meet for drinks and colour the night for their eyes only. :-)
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** I am normally not a praying man, but if you are up there, please save me Superman **
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