Regarding my own mother's things, I am very lucky. She painted for years -- big oil paintings, mostly of buildings. Her main job was as an advertising copywriter but her paintings were not amateurish. She used to display them in exhibits and juried shows. In high school, I became friends with a girl whose parents, I later discovered, had one of my mom's paintings hanging in their house.
I really like the paintings and have them all over my own house. I have a few other things of my mom's, too, but whenever I have to get rid of anything of hers I don't feel as bad about it knowing that I'll always have the paintings. They meant more to her than a vase or something.
Yesterday a couple of friends came over to do some small repairs around my house. The man, a friend since high school named Terry, sidelines as a handyman. When he left he said that when I die he wants the painting she did of a porch, from the perspective of someone on the porch looking out on the ocean. I said I'd put his name on the back and I think I'll do that. My brother will probably take most of the paintings but wouldn't begrudge Terry, who is his friend as well.
Of course we don't know which of us will go in what order. Terry smokes cigarettes, but he's in better shape than me. It's sad how when you pass 60 you start thinking about things like that more seriously. But then, any of us could get hit by a bus at any time.