Watch collecting are seen into a hobby. Just like a toy can resell for a lot, so does watches - however the nature remains similar as well, it should be sold to community that appreciates it - hence, not every country has market for some watch brands. As it's a hobby, the biggest value comes from taste - when you like it, the value increases. Hence, my thought about it is that it depends on whether the buyer is able to appreciate sentimental, historical and refinement in the watch, especially in higher price tier.
Same watch, similar performance, but different mechanism - some people can appreciate that, some can't.
Similar looking watch, different finishing - some people can appreciate that, some can't.
That kind of thing.