Demand and supply. Many people want to be associated with wearing a Rolex piece. It's well-known to the general public and holds its value well. It's a sound purchase. Period. I remembered when I advertised an Eii some time back, there was a chap whom tried to convince me to lower the asking price by some 20% telling me that it was a buyer's market and that he could get other GMT watches at much, much lower prices but the function was the same. I then advised him to go for the "other GMT watches" to save the monies. When the Eii was sold off a couple of days later, he had the cheek to come back and claimed that I should have negotiated with him and that he might have eventually pay my asking price. I informed him that there was no need to do so, as i know that a Rolex sells so it was not necessary to negotiate to and fro. If it was a Tag Heuer or Oris, then probably the negotiation process was necessary.
There are far more complicated and expensive watches than Rolex, but the market could be limited to watch connoisseurs so flipping could be relatively slower. Anyway, watch prices were relative to one's consideration. Consider the new Sky-Dweller in s/s and WG- I think that it's an absolute steal at RRP : RM58k before GST, in relation to its complication and previous precious metal pricing. In fact, I am looking at some consolidation to build up some funds towards the piece if I could get it without premium. Plus I know that it would hold its value over time. Another chap told me that the same monies would be better-spent on a Hublot Big Bang; but personally, it does not speak to me. So the Sky-Dweller would be over-priced to him but not to me, ditto the Big Bang vice-versa.