They switched [1] as early as 1977 to Seiko after a brief flirt with Breitling, then to Omega from 1995 although Rolex did briefly reappear in 1989.
In other words much of today's target market did not see Bond wear a Rolex in cinemas, and it is a testimony to the strength of Rolex's brand that Omega's own product placement has been hijacked in people's minds.
They lead the game in terms of signalling disposable income to the 90%ers. They have been beaten by the Japanese in multiple areas for decades.
The best example is that the Swiss used to have accuracy contests which they had to cancel after Seiko systematically bested everybody else for several years (easily Googleable e.g. [1]). Even in the quartz world, the current best is still Japanese with the (comparatively cheap!) $1,000 Citizen Chronomaster, the most accurate non-atomic-sync watch. And your average $80 G-Shock now has the atomic sync functionality.
How about extremes? Whilst everybody else was messing about with fragile and expensive helium valves to deal with coming back up from high pressures required by professional divers, such as those repairing oil rigs, Seiko put together an R&D team and after 8 years of research came up with a design that went deeper with no valve, the 6159 aka "tuna can" [2]. Of course divers now use a dive computer, but if you need a backup the Darth Tuna is very good indeed.
Want some real "handmade" artisanal creds, some ties to history? How about hand painted laquer dials using centuries old traditional methods (see any "urushi" model) or the extreme attention to detail in the Credor line (e.g. [3]).
So the watch world is fragmented into Seiko lovers and haters, the former seeing value in the engineering and artisanship and the latter seeing a lack of brand equity and disposable income signalling that is more easily found in Switzerland (or rather, on what is badged as made in Switzerland, see [4]).
Maintenance costs are not per se an indication of low quality. For example, Seiko's Hi-Beat movements (which "beat", or move the seconds hand, many more times per second than average, generating the illusion of smoother motion) have an exceptionally strong spring and need more frequent servicing as a result of the extra work done by the movement, whereas a $10 vintage HMT watch from the 1970s beating 5x slower might just need its first oiling which you could do yourself.
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.
It's very simple in Singapore too, arguably simpler. You go to the Small Claims Tribunal (you can get a date within days, anecdotally), the Registrar decides the claim in a few minutes, and it costs you a total of 5 quid to file the claim. The whole thing takes a couple of weeks at most [edit: or a day - see 1].
I think something similar exists in Switzerland, but the (German) landlady correctly guessed that as a non-German-speaking foreigner, I would not take the time and expense to attempt it. Imagine attempting to contest the necessity of "dusting the sides of books on bookshelves" to an arbitrator in a foreign language...
Are you sure about the rent? I rented a 2 bedroom, with windows on 3 sides, next to a park and public transport, and a large balcony with BBQ, for 2 months (so short term let, higher rates), 20 minutes by tram from my office near Seefeld, for 1,500 CHF/month.
The landlady did keep my deposit (sorry, "had a professional cleaning done for the exact amount of the deposit", and sent me the detailed list as proof in German which I do not speak), bringing that to 2,250 CHF/month. A quick back of the envelope on real estate inflation since then brings me to around 2,500 CHF/month (1,700 CHF/month if you ignore the deposit trick).
That's not as cheap as a small town in Europe but it's quite cheap, I think, for a major international city and definitely when you take into account the starting salaries. Vaguely remembering, a graduate from a good university starting in strategy consulting could expect 90-110,000 CHF/year in Zurich vs 35,000 GBP (49,000 CHF) in London despite higher COL and higher taxes (same companies, which may or may not start with M or B). I have no idea about the numbers in San Francisco but I bet they are not so good either.
There's other issues with working in Switzerland if you come from Anglo-Saxon big cities, but COL isn't it if you are paid locally, unless you are dealing with an employer exploiting the unemployment rate in your home country to underpay you substantially (which is definitely the case with some French speaking companies in Geneva).