Over paid for the Rolex in the long run?

[aaamax]

A lot of talk about high prices lately and it got me thinking.
Has anyone truly ever lost any significant money on a watch? Let me preface by saying that flipping a new watch shouldn't count for this tangent. To be more true to the this concept the question should maybe be:
"After 20 years with a watch has anyone lost $$ when they sold it?"
I can say after many years and many watches not one would be sold at a loss.

And with that my friends, I now have a good excuse to pick up a new WG SD… Lol. Lets call this "self-enabling."
Cheers.