We're redoing our will and it's forcing me to confront something uncomfortable: my sister is doing well financially, but my brother has always struggled. I know leaving different amounts to each would be fair in a practical sense, but it feels like I'm judging their life choices from beyond the grave. Part of me worries that equal shares just reward poor decisions, while another part remembers our parents always said they loved us the same. Is it fair for a parent to give unequal inheritance to adult children based on their financial situation, or does that betray the principle that a parent's love shouldn't be conditional on how successful you turned out?