THE DIAMOND MINES AGAIN: I was totally fascinated by this Slate piece on children’s books about poverty or “financial ruin.” I would recommend any Ramona book to anybody, but yeah, Ramona and Her Father is heart-rending and wonderful.
Of course if ruin is what you’re looking for, A Little Princess is the best possible choice; I would also add all of the Blossom Culp books, with their scrappy protagonist whose momma boils roots to eat, and Jane Langston’s Transcendentalist tale The Diamond in the Window, in which the whole narrative is driven by the children’s desire to save the family home.
I wrote about The Toothpaste Millionaire here, and would recommend the same author’s Pushcart War. Also would recommend the Henry Reed and Great Brain books, and Own Back Ltd., published in the US as Witch’s Business. The HR and GB books are more about capitalism and creativity than about poverty really, but OBL is fairly hardcore about the intersection of business and inequality.