To be honest, I haven't read the whole thread, but I'll put in my 2 cents
I think it really depends on how conspicuous 'you' are.
People who know watches will, in my case at least, either be interested or appreciative, rather than judgemental (I'm way more judgmental of people wearing fake gold/fake rolexes/fake diamond whatevers and trying to be flashy). Most people won't even blink an eye.
I have a Rolex GMT Master II (stainless) and an Omega Seamaster 300 (Spectre edition).
More people realize what the Rolex is, but I don't get many comments on it, and if I'm wearing it with a suit or jacket, it's usually tucked under the sleeve, not sticking out. A friend of mine who I've been hanging out with regularly the past 5 or 6 months was talking about one of her friends who loved watches and Rolexes, when I said that I have one and wear it every once in a while she had no idea I owned one.
The Omega looks like any other wristwatch whether it be $10 or $10k and with the NATO strap, unless you see the movement underneath or really hold the watch, nobody would have any clue what it was (minus a true Bond fan or watch aficionado
)