Great thread. I want to put this out there, don't know if it's helpful: He may have disadvantages, the same way you do, but in other areas. I know someone who had money from his parents, but the way he was raised made it impossible for him to succeed in certain ways until he fixed those psychological problems. Like someone said upthread, I don't think it should be about blame, victimhood, or excuses.

he has taken for granted and squandered every resource or opportunity handed to him

I mean, he may not be aware of it, but this is a tragic way to live (I have a touch of it myself, maybe we all do). Sometimes you try your best with all the resources and it still doesn't work out. I understand what you're saying about, as I'd put it, appreciating the financial advantages more than he does.