Was it ever worth the price?

Any luxury watches in fact , Maurice , Jaegar , IWC etc

I'm from a somewhat modest , middle income family hence I was never really exposed to luxury goods, and I'm never to keen on them.

When it comes to personal spending I've always been frugal. Buying 2nd hand stuff , eating food on a budget ( though I eat a lot since I do train upwards of 5x/week).
I don't drink nor have a nightlife... Since I never see them as a good investment of time and money
Lately my business is doing somewhat decent. And I'm able to save a decent amount of money a month. Last year I was able to get myself a 2nd hand car. Which I'm really proud of.
And lately I've been looking into luxury watches , partly cause I was exposed to my client's collection of watches which well ... isn't good

I'm thinking of getting a Rolex for my 25th Bday , which is next year.
I don't wear watches so my main idea of getting a Rolex is

1. Hopefully it appreciates or at least retains 80% of it's value over the course of 10+ years

2. Pass down to my children

3. Add a little swag ... I guess?

I'm thinking of a moderately priced 2nd hand Rolex say a Datejust from WingWah , apparently I can't get a brand new Rolex as the waiting list is 3 freaking years.

So what do you guys think.

Would a Rolex be a good ( or at least decent ) use of money?