-
Part of that is because Rolex are doing a much better job of protecting their brand. There are few discounts available, they're limiting their product range to watches with a long design life, keeping supply relatively well aligned with demand, allowing hardly any grey market stock and constantly raising prices. As a result most Rolex's change hands for not much less than their sale price. Compare that with heavy depreciations for Omega where the grey market means you can automatically get a heavy discount even on new so used prices are weak. Don't get me wrong, I love my Omega (pre '75 when they made good quality watches and before they had to be bailed out). They're losing money year on year, it wouldn't surprise me if another bailout was on the cards.
IDK man, buy what you love. A watch isn't an investment grade asset as there's too much volatility. I just think it's a bit reductive to say that a vintage railmaster costs a lot (and a new one doesn't) because the cost of owning a vintage watch (if you can afford to tie up the capital) is probably negative.