I know I'll never understand it and I'm sure if I was a billionaire my feelings would be much different given the change in perspective, but for me my dream boat is the biggest one I can sail and comfortably handle with 2 people. Once you cross the threshold into needing a crew just to even go for a day sail, then I'm not interested.
Now a maintenance crew when in port is a different story, that I am happy to hire the help for with a larger boat, but sailing, handling, docking, mooring, anchoring, etc... should never be more than a 2 person job in my book.