The story behind a watch means so much more than what the actual watch is, or how much it costs.
I will eventually be passing on several 4-6 figure watches to my children. What they do with it matters little to me. If they choose to sell it, and put the funds to something that means more to them, by all means. But the one watch I expect them to treat with the respect it deserves is my G-Shock DW5600 that was gifted to me by my parents for graduating law school.
My parents aren't wealthy people. But they made every sacrifice, happily and willingly, to ensure that I had every advantage in life. When I graduated we were in no position to spend the $100 on something so frivolous like a watch, but my parents did it anyways, because they remembered that I had wanted one since I was little, but they could never find room in our budget to justify it. So the G-Shock is much less a watch, and much more a celebration of my parents, and their selflessness.
And that's why it's the one watch in my collection that will be passed down as an heirloom. That, and that it'll likely outlive my bloodline.
I'm afraid to admit this, in fear that I'll get flamed by the community, but I too don't wind my (albeit, automatic) watches. Nor do I use my watch to tell the time; as I still take a second or two to tell the time reading an analogue watch. I also switch my watches in and out too frequently for the power reserves to hold up.
So, perhaps in the past year or two, I've just stopped setting my watches all together. I just don't see the point.