The Wealthier One

In response to mr. sjrjala's blog, my answer would be Bill, hands down.
I think it's more important to be wealthy in health, family, and friends than it is to be wealthy in money. It seems like money can do ugly things to people and Bob sounds like he should be miserable. Bill, on the other hand, has a family to keep him company and that must serve as motivation to keep going. If he can keep food on the table and clothes on their backs, he's not doing so bad after all. Bob won't even be able to share a meal with his family or see what clothes they're wearing. This is all from a family stand point, but if someone was more materialistic, Bob would take the cake.