Having flip quite a few watches todate, I would also chalk in that Rolex (I qualify, selected sports watches) seemed to hold its value well. If you have the holy trinity in its collection i.e. Submariner, GMT-Master ii, and Daytona; you should not have any issues getting back your purchased price after some time; given that these models tend to appreciate pretty well. However, the same can't be said about Datejust, Day-Date, Milgauss, and the likes. And sometimes, other elements come into play. When I had the SD4k, the secondary pricing was relatively low but once it was discontinued, it went up quite substantially and there were also a surge in demand suddenly.
Check out the pricing for PP Nautilus and the premium that BNIB pieces were doing over the MSRP. At the end of the day, it's all about the demand and supply; and if you like certain models and they in turn are part of the highly-demanded pieces in market, then you could have your cake and eat it too.