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The 2nd set of watches you showed are over priced but I don't think the first one is that off the mark with the MOP face. The other watch you have on your hand can be found for less many other places.
As mentioned, it's the stretch in the band that will bring down the price, not the age of the watch.
May I ask where you saw these watches? NYC in diamond district?
If you want a great price on used Rolex, try to go to a jewelry and gem show. They bargain!!!