When I'm dead ,I won't give a $hit about all my stuff....I'll be dead...........I give away as much as I can now.
Most of this stuff will last longer than we will. In some cases, several times longer. We should think of ourselves as stewards, to use and care for it, until we pass on or lose interest, just as we would a homestead. Then, it should be forwarded (sold or given away) to someone else who will use and care for it, not tossed in the dump.
You don't have to clear out your inventory while you are still alive and active and thus deprive yourself of the benefits of it. It's not that difficult to let members of your family or your circle of friends know what is not junk, that someone else might appreciate it after you disappear off the earth, and leave behind some kind of contact information.
A lot did go to the dump in droves back during the 70s and 80s, as the old timers who grew up in the 20s and 30s were dropping like flies. Unfortunately, at that time, the interest in "vintage" hadn't caught on and the AM come-back was still somewhat in its infancy, and most hams on the air at that time had swallowed the "state of the fart" and "new is good; old is bad" propaganda hook, line and sinker.