I love your selections, especially the one watch- two watches - three watches series.
Problem is, I can't stand steel bracelets, and some of the best happen to be mainly, or only steel bracelets.
Second, I don't like 'technical' watches (driving, athletic, swimming, diving, aeronautical, ocean racing) the exception being trekking specific watches. The reason is that I feel like a phony, wearing these (only the trekking one is OK, I do go on treks, say, once a decade).
Third, for daily wear, there are four faithfuls: one each circular dial, with black and tan strap; one each rectangular dial with black and tan strap. The straps have to match my footwear; for trainers or canvas, I have my Casio G-Shock, which hangs on my wrist like a grandfather clock.
On special occasions, I wear either one of my grand-dad's manuals; I am really fond of them, even down to the winding and setting.
Somewhere during my twenty-odd changes of residence, I lost the old golden half-hunter pocket watch, also an inheritance from Granddad.
Live moves on.
If I were buying today, price no consideration, it would probably be a JLC reverso. Or a Patek Philippe, perhaps a Calatrava? A little lower would be an Omega De Ville. As a second watch, as a distraction for evening wear but not with black tie, a Rado. A tempting one would be a Tank Americaine, Even less would be a Frederique Constant, a Slimline. Stuff cheaper are not legacy watches; they are more or less junk watches, some priced more than the others. Those are the ones I earmark for wearing with tan shoes, with black shoes, for casual wear on social evenings.