Superdoc explain it very well. Rolex holds value very good. But NOT Yachtmaster. If you want to bet Daytona, Submariner and GMT are the ones to go. If I were you I will try to find 1-2 year old Planet Ocean (with 2-3 years warranty intact). The resale value will not go down too far from your purchase value and you will get the watch with young and modern model rather than old Oyster case looking.
Seriously, high end mechanical watch build was so good that they can stand 40-50 years of wear, so buying 1-2 year old high end watch is almost indistinguishable from the new one (except some very fine surface scratch that you will get within a month of wearing it anyway).
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