From a guy who has been collecting watches for about 15 years, I'm still torn by the "Rolex thing". Beautifully finished watches? Without question. Well made? Certainly. Hold their value? Check. The best watches in the world? That's where things get fuzzy.
I will undoubtedly keep coming back to Rolex now and again, consider one, then buy something else. I just can't get past the fact that if you took "Rolex" off the dial (and apparently every other surface of the watch these days....), would I pay $8500.00 for a steel watch with a good Swiss automatic movement? No. With that said, I do struggle with the same question for a $2000 watch. What's in a brand? What is status? Do you want to know that what's on your wrist is the best thing in its category in the world? Or, do you need others to know(or think) that what's on your wrist is the best? When you ask someone who knows nothing about watches what the best watch in the world is, they will, 9 times out of 10, say "Rolex". When you ask a master watchmaker the same question, opinions vary widely. Whose opinion would you put more stock in?
Apologies for the stream of consciousness style, but it's always interesting to kick this question around again. I've owned three so far: Sea-Dweller, DeepSea, and a no-date Sub from a while back. Enjoyed them all, sold them all. The fact that it said "Rolex" on the dial was never enough to keep them interesting to me.
Final thought: Why is there such a deep coolness chasm between Sean Connery (or Jacques Cousteau) wearing a Sub in the 60s and a fat guy at the blackjack table in Vegas today?