I have not gotten to that point yet, but I think about it
As I have no children, nor does my wife, there are a couple of nieces and nephews, the ones on my side I have only met once and since my sister is a raving communist ( Harvard educated you know) that rules them out.
Wife's nephew held some promise, he used to ask to be taken to the range for his birthday.... never got any more interested than that, plus he lives in MA.
Assuming I die here in Fl, and not in NH.... at some point we will sell the NH property and become FL residents, it is going to be a huge problem.
Besides things that may have been declared lost in a boating accident, I have a lifetime of tools here, much of it is Snap ON, MAC, etc.... I have showed my wife things like the 1/4 inch ratchet that currently sells for $100 dollars.... these are not the things you sell at a yard sale for $5.00.... there is probably 50K in tools in the garage and I'm not selling them while I am alive.
Plus the cars and motorcycles.... those can be thinned out at some point but I said I will never sell the bike that belonged to my late best friend and I have an idea of who I am going to pass that down to.
the running joke I have with my wife is don't sell anything for less than twice what I told you I paid for them.
What do you do with 1500 compact discs?