As long as the HOS is paying out of his
personal pocket, I don't care if he spends $100k
Looking at some sample F fares from the east coast, it might be in the range of $3k/pp ... so for a family of 4, nearly $12k ... relatively to his salary, I would probably do it?
Let's hope he used a good miles-earning CC for the bookings
Welcome to FT, btw! ^