It's really difficult to predict and has to be managed well by the company. But a big one is when a model gets discontinued because at that point no more will be made so supply is fixed.
So the current generation of professional (ie steel) Daytonas have a ceramic bezel. This is to avoid scratches but means they can shatter with enough force. The ceramic itself is baked in a plasma furnace. The tech behind these things can actually be really cool.
So Daytonas have historically sold above MSRP on the secondary market but not by this much. About 10 years ago the new ceramic Daytonas were released and what happened was a lot of people sold their previous DAytonas to "upgrade". This meant that what was 6 months earlier a $13k MSRP watch was selling for $10-11k and that seemed crazy to me given it was now discontinued so I bought one. At the peak of the market, that watch would sell for $30-35k. Now it's probably under $25k but that's still a good investment.
But steel Rolexes never really appreciate that much because the volumes ard really high. You're not going to get rich buying a steel Submariner. There's simply too many of them out there.
But one exception is the really vintage Daytonas, particularly what are called Paul Newman Daytonas [1]. These were watches that back in the 1980s sat in a display case for years (at $500 or less) because no one bought them but an association with Paul Newman skyrocketed them in the public consciousness to the point that a 1960s era Paul Newman Daytona in mint condition can easily be worth $500k-$1m+.
The market dynamics are really fascinating but it's now become essentially impossible buy an in-demand watch from an AD unless you're a big spender on other products there (they're all typically jewelers as well). The history of Rolex was in utility not luxury (eg the GMT was invented for Pan Am pilots who suddenly were flying cross-country, the Submariner is a dive watch, the Daytona was originally for racing drivers, etc).
[1]: https://www.bobswatches.com/paul-newman-rolex-daytona