That is easy. Both my sons know what I have and what it is worth. They both work on cars, one son restores cars and motorcycles and the other hot rods modern iron and likes to make piles of sawdust. Both have expressed their desires and know what the other wants. They know the rules, any arguing and it goes into the sale pile.
Sometime within the next year or so I will have to go through a 80+ year collection of tools from an airline machinist. I will be the one going through it and will be parceling out stuff to my sons and brother. I know the value and know that it will be going to someone who will use them.
I figure I have another 20 years but you never know. Last Friday I stepped into a hole and fell back mashing my head against a concrete wall. I was sort of out of it for a couple of hours but I slowly came back around and now all seems OK.