There's no doubt about it: our protagonist is poor. Dahl never lets us forget it. Why make him so poor? Why not make Charlie just be an average kid in suburbia, with a dog and a wagon and a backyard? Well, we think it might be because Charlie's relative poverty at the beginning of Charlie and the Chocolate Factory makes the riches he is given at the end all the more sweet. His poverty makes us sympathize with him, especially when you consider the fact that so many others seem so rich. And that sympathy builds when we learn that he's really a good kid, too. So when Charlie is the last kid standing at the end of the tour, we're elated. Plus, don't forget: Charlie hasn't won any money. What he's won is a home, and an endless supply of food for him and his family, which makes him the richest kid of all.
Dahl shouldn't have made Charlie so poor: it makes an otherwise happy book seem way too sad.
Charlie's poverty is the only reason we root for him. We just feel bad for the guy.