I think for any item to be collectible there has to be some supply for people to collect.
I do not think that there are that many Rolex sponsored sport event winners for one,
secondly how many of these want to part with their trophy prize?
These Daytona or Rolex Cup prizes are different than Rolex watches issued to Iraqi secret service, Italian Police or Vatican Air Force...
They were awarded for achievement and sanctioned by Rolex. Not given away to some cronies.
This is the reason that I believe them to be rare.
It is not easy to become a member in the International Maxi Association. One has to be sponsored by a member and one has to have money to afford big yacht and running it.
The Submariner that I am now an owner of was awarded for a Maxi Yacht race sponsored by Rolex
and most likely, based on the rules of the race piloted in large part by it's owner James Dolan.
He is an owner of N.Y. Knicks a director of Madison Square Garden and a media magnate.