Wow. He doesn't even care that he can't get seating together for his family of 5 including little kids? And assumes that United will take care of him? My own brother can be an idiot sometimes too, but he if gave my family a free upgrade to Hawaii, I'd be all over it.
Don't try and get him an upgrade at the hotel. He'd be very happy with the small room overlooking the roof rather than the suite overlooking the ocean.