You are perfectly describing the issue when sorting out a hoarder‘s stuff. There‘s no way of knowing what‘s precious and what not for most of the things. There might be some obvious things (wooden furniture / ISO documents that are still relevant), but the rest goes in the trash usually.
> One day when I'm gone, maybe they will enjoy going through them
My mother used to say the same thing. But I‘m not looking at that old stuff, ever. Maybe your kids will. It’s your decision whether it’s worse to be false negative or false positive here. If the stuff is not taking up too much space, it’s probably a good idea to keep it. Hoarding is something else though.
> One day when I'm gone, maybe they will enjoy going through them
My mother used to say the same thing. But I‘m not looking at that old stuff, ever. Maybe your kids will. It’s your decision whether it’s worse to be false negative or false positive here. If the stuff is not taking up too much space, it’s probably a good idea to keep it. Hoarding is something else though.