This may or may not hold true into the future. While it is true that Rolex has held its value really well over the post several decades it is certainly possible that this won't hold true into the future. I think a good argument could be made for why it is unlikely to continue as it has in the past. A lot of Rolex appreciation in the pre-owned market has been directly related to how Rolex has changed their pricing at the AD. If you look it up, you will see that in 1960 a Rolex sub cost $150. Using 3.25% inflation (which is the average I found when I looked that up) adjusted for inflation that same Rolex should cost $1022 today but instead it costs roughly 10k.
Will Rolex be able to maintain the aggressive pricing increases that they have in the past? I guess only time will tell.
Idk about this....
I have bought and sold dozens of both Gens and Reps. My experience with buying Gens is that if I buy new at the AD I can expect to lose a minimum of 25% the minute I walk out the door & some brands it is A LOT worse. (excluding Rolex) Say you buy a relatively modest Oris for 2k, you are going to take a minimum of $500 loss to sell it & more than likely it will be significantly more.
With Reps my experience has been that I rarely lose more than $75 if I decide to sell when the watch is in good condition.
As a general rule, watches make extremely poor investments (including Rolex)
The issue is on the popular models, there are constant updates that render the past version "obsolete".
I've a Noob v10 for sale right now. I bought it new for $480, all TDs now have dropped the price to $330 because new version is out. There is no way I can sell it for more than $300.