That brings back a lot of memories; if you were a New Yorker for as long as I was, the City never leaves you. Just to the west of your shot is the Paramount building with the clock tower and globe ornament. Although not the best known or biggest tower in New York, I think that building is emblematic of the glory days when radio, tv, and film were all going strong.
You are entirely correct about the bling factor; for the most part, when it comes to watches, New Yorkers are about the wow and status factor, ergo the preponderance of Rolexes, Breitlings, etc. Unlike in Europe, there does not seem to be a collectors "ethos" except for isolated individuals. Like you, I always had my eyes peeled for Heuers and rarely came across them even at the vintage dealers. I also cant recall seeing a single vintage Heuer on the wrist of anyone in Manhattan except for me, and that includes 20 years of commuting via every form of transit imaginable and walking the streets daily!
I remember once an Italian couple staring at me for a whole Amtrak ride from Boston back to New York. Close to the end they finally came over to tell me how fantastic my Calculator was--no Americans ever even noticed the watch...