The question that the narrator of "Why, You Reckon?" wonders about is, "Can money buy happiness?"
The answer that the story proposes to the question is, "No, money can't buy happiness"
One detail from the story that supports this answer is the incident when two poor black men connived to rob a rich white man; they took everything they could - his money, diamonds, shoes, coat, and so on. The rich man was not in any way upset about being robbed; rather he was very excited. He said "This is the first exciting thing that’s happened to me... This is the first time in my life I’ve ever had a good time in Harlem", thus showing that money, for those who have a lot of it, is just something disposal, not important.
