I have seen and experienced people bragging about their Rolex, telling my wife she should have gotten a Rolex like theirs instead of a Cartier because Rolex has better re-sale value. Asking me what kind of watch I am wearing ? Where is your Rolex ? I feel if I got a Rolex, I would be "joining the club", which is totally not what I want to do because I really dislike that kind of behavior.I think the idea of a Rolex (and a Sub in particular) being a bragging-watch is a bit exaggerated. Yes, on watch and clothing forums people believe they can determine someone's personality by the watch they wear (and there's plenty of people who have spreadsheets detailing the average time on a waiting list, value increase, and so on..), but you can also get branded a heretic for choosing the wrong weight of selvage denim for your jeans. It's not really a good indicator to what your average person thinks. If you were to wear a Sub in public, I think the most common reactions you would get is "Hey man, cool watch.", "Well, SOMEONE is doing well for himself!" and "Is it genuine?" Rolex IS the most recognizable luxury watch brand out there; my mum, who wouldn't know a Patek from a Casio knows that Rolex is fancy, and that alone makes it a bit of a style statement. But in my experience, most people aren't grinches who will hate you for your success, or think you're trying to put yourself above them by wearing a nice watch. The handful that would resent it sounds like jerks who you probably don't want to know anyway. I'd consider it an extra feature on the watch: "jerk-detector". Let's see an Apple watch do that!
That said, I WOULD worry about the inflated prices, and the fact that the watch being so recognizable means that a punk who wouldn't look twice at a Vacheron Constantin will instantly recognize a Sub, and knows it's worth stealing.
I prefer someone compliment my watch itself vs. the brand. I like having watches and watch brands less known and less common than Rolex. I like to be a little different and visually, I like other watches more than Rolex.