On the subject of Rolexes, pile of poo!
I'm afraid I just don't "get" watch one-upmanship. Its a tool for telling the time, I just can't manage to view it in the way I might a camera or a cycle. It either tells the right time, or it doesn't.
It's not one-upmanship for everyone, some people just like the quality and aesthetics. You can say the same about all sorts of things: shoes, cars, rucksacks, houses. We all value these things differently.
Your cost objection is also a bit of red herring. I know it sounds odd, but you can own almost any of the Rolex tool watches (i.e. the sports models) for very close to bugger all...
I've just sold one of mine. Owned it for about 5 years, not been serviced in that time and had been worn plenty, so it was rather scratched and in need of good wash and brush up. Sold it for £5500, which was more than I paid for it retail. So, I've owned and enjoyed it for years, and now it has returned all my money to me. The one on my wrist is just the same, it's worth far more now than it cost me, so any time I want my money I can walk into the nearest dealer and get it all back on the spot.
You can't say the same about the cameras or bikes you mentioned you were happy to spend your hard earned on.