The today's high-end lover/collectors seem to have entered this world from "inside". Some I asked or have met mentioned that they started having interest in watches from the internet or books or magazines. Then they started studying more to details - history of the brand, what is the movement and who designed it, when, where, and such, for example. Then they start collecting. Sure, they start off from the relatively affordable ones, but they do have in mind what they want from this hobby. So, "going up the value chain" may not be the right word. Of course, some people enter the same way, but some are rich already and climb up the ladder quickly, but both types know what they want or expect from the watches and are happy with what they have within their means. Did I answer your question?
Ken