Having travelled with a number of “high profile talent” my experience is that c/in agents, lounge dragons, gate agents are often more worried about not appearing to be “star struck” when engaging. They tend to just get through the process as quickly as possible with allowances the least of their concerns.
I will add, none of my lot have ever tried to “game” the system. They know the guidelines and just want an easy journey. Saying that, when you’re escorted by BA SS you could quite literally bring the kitchen sink onboard and still be asked if there were any other items needing stowage.