> it looks great with a tuxedo
Debatable, as it is a sports watch (arguably "the" sports watch). Wearing a sports watch with black tie suggests a middle class New Worlder. I happen to like these values (meritocracy, individual rights, equality of all before the law) much more than the alternative so see it as a positive signal. Also, (see [1]) signals ought to be true or the effect will be very negative, since nobody likes a fake, so better the sub with the "tuxedo" if that's "who you are".
The core value of a Rolex over other brands is two fold.
First, the company is ensuring that the value of the watches will never drop through limiting grey market availability and limiting supply generally even in the face of increasing global demand (people now complain about months-long waiting lists for special editions). As you point out this does make it a sort of global gold standard in terms of maintaining value and fungibility.
Second, it shrewdly invests in multi-generational, tightly integrated marketing to maintain the image of the brand in the global lower and middle classes' mind as "the" luxury watch, as well as in the target market (the GP piece is an example).
AFAIK it is the only brand that does it so thoroughly; Patek has similar operations (including bidding on its own vintage stuff, which even involved setting up a museum, to drive prices higher) but targeted at the aspirational upper middle class only [2], and the other brands are considerably less well recognised or not perceived as expensive. This investment in marketing builds "signal equity" for Rolex wearers in that everybody will see it, not just the readers of Hodinkee.
Which is why I disagree with you that:
> it doesn't scream "expensive"
To close on a humorous note: http://www.gq.com/story/male-engagement-ring-rolex
(I would, personally, blow my $50k on the new Laurent Ferrier Montre Ecole. /signalling)
[1] https://www.quora.com/Why-would-anyone-buy-a-Rolex-watch/ans...
[2] http://thelastpsychiatrist.com/2011/11/luxury_branding_the_f...