Actually, to me, being mostly a vintage watches type, most of the joy is in the hunting of the rare, under-appreciated timepiece.
This year, I have found myself selling a watch that had a significant monetary value (more than I would ever pay for a watch as a buyer), just because it didn't feel right to me to have a single watch worth that much.
I have many other watches that are far less known to collectors circles, and therefore far less 'valuable' moneywise, but I am somehow proud to have found these 'rare birds' that I (and inner collectors circle friends) truely appreciate for what they are, which are not less (and usually even more) interesting than the 'valuable' one.
When a watch reaches a certain market price, to me it becomes a worry, or I don't value it moneywise as much as others do, so I'd rather sell one fairly visible 'collectible' watch, than sacrificing 10 far less 'appreciated' watches for about the same value.
So, to answer, I'd rather sacrifice one 'recognised' timepiece, and use the proceeds to get multiple under-rated watches which are fairly unique / difficult to 'hunt', and in which only few see value in, rather than giving up on multiple watches to get the pricey - because 'most wanted by the mass' - one.