The man can easily afford the money, and a parent can't deny their kids medical when it's popcorn money to them, but those women would be much better off if they started standing on their own two feet.
Edit: BIG EDIT: I was talking about the Wig. I glanced right over Booey's name. That is a lot of money. He could be insuring an extended family or he might be in a high risk group pertaining to his brothers sad demise. Or he could be lying.