TLDR; Michael Norton did the survey of people with networth > $1M and most said they need 2 or 3 times more. People with networth > $100M also don't feel satisfied because they tend to answer the question "Am I better off than last year?" by comparing to other folks who did even better than them.
It looks to me that if you are in $3M to $10M bucket, you have financial freedom to live low key upper-middle class life. This is what Tim Ferris refers to as "New Rich".
However when you are above $10M, something else happens. While you have financial freedom, you are also just starting to taste freedom of will. Sooner or later it might get annoying that you must wake up at 5 AM because that's the only flight available OR that you can't get the penthouse suit because someone more wealthier decided to book it out for entire year. You still depend on publicly available utilities fiercely competed upon. Unlike your peers with $100M you can't own GulfStreams or have $25M Malibu mentions overlooking Pacific with infinity pools.
When you get to $100M, things change again. Now you do have little gulfstream but it's far cry from private 747 with king size bedroom, office, bar and a chef. Sure, you got that mention in Malibu but that large paradise estate in Hawaii with its own beach and waterfalls is out of your reach. When you meet your billionaire friends in blue waters of Greek island of Creet, your little yatch looks like baby's first toy missing things like its own sub and helipad. Life is good but not that good because resources at your disposal have still limitations to achieve maximum possible freedom of will. People tell you how awesome you are but you keep finding new limiting ways you are restricted to act by your will every single day.
I think its only above $3B that you are in realm of pure score keeping, the quality of material possessions cannot be improved further and freedom of will is pretty much maximized. Now you are truly limited by time, and much less by ideas. So until you get in to that top 1000 individuals, it's going to sting one way or another.