I guess it's just down to luck that a particular model you bought 20 years ago now fetches a high price. You wouldn't have known at that time you bought it. It doesn't happen for every 20 year old model.
However, buyers of current models will not be so lucky cause I doubt any current models of rolex now will escalate tremendously in price in 20 years (except due to normal inflation) because any rolex models now are produced a dime a dozen. Even for the short run (and hence limited numbers in the wild) Day Date 2 (41mm), would you dare say it's surely a high priced item in 20 years?
A Year 1980 Rolex in Year 2010 (30 years old) is different from a Year 2010 Rolex in Year 2040 (also 30 years old). Unless WW3 happens and a majority of Rolexes get wiped off the face of the earth, then it will be different 
In the word of the Great Joker: Why so serious?
True WIS don't view watches as hedging/investment instruments anyway...if it does appreciate in value, then great! If not, who cares - just staring at the collection gives the WIS an orgasm already!
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