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It's a very specific niche of hated watch that becomes valuable I've noticed. You need a weird/undesirable color on an otherwise desirable watch such as a yellow/pink/blue OP. A watch that just genuinely has little interest such as the Milgauss just fades into relative obscurity and the prices changed maybe $1500 since being discontinued, and I haven't seen any actually sell at the "new" pricing, just asking prices.
There are definitely many ways to own expensive watches for the long term and not have them cost you a bunch of money, but to buy them thinking they will actually appreciate beyond what a stock portfolio would do is basically impossible - the watches that might do that, you and I will not get our hands on at close to MSRP.
TL;DR is buying any Rolex that you love and want to own will likely cost you very little - a 20 year old Daytona similar to mine sells for about what I paid for mine. But that's not an investment, that's just a less expensive toy than something that isn't worth anything later on.
-Mark
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I'm old now - boring street cars and sweet race cars.
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