If it has meaning, then keep it. If it has meaning to someone else in the family, let them have it. If it's something like Grandpa's old ladder that means nothing, get rid of it. Turn a buck if you can.
A cautionary tale, if I may...
Some years ago, when my Great-grandfather died, he specified that all his Masonic gear (his ring, Past Master's apron, etc...) would go to my father. Since we live a fair bit away, it was given in trust to my great-aunt, and dad would get it whenever he was in town. Last year, my great-aunt died, after a long illness. Going through the house, he found that all that stuff had been sold. A Mason's ring (at least a simple one as this) would sell for maybe $40, but my uncle who had POA sold everything of any value, including many family heirlooms.
If there is something of value, or just something of sentimental value, it needs given before the person dies. Otherwise, who knows what may happen?