Nobody who uses this strategy will come even close to spending every dollar that they earned, they spend all they want yet still end up leaving all their wealth to their kids when they die.
The FT runs a magazine called "How To Spend It" with ideas for what cheeky stylish thing to buy this month after you already spent it on what you want to. That this is apparently a lucrative business possibly tells you that you can max out your quality of life and still have money leftover.
Really depends, I can see a lot of quality of life on leaving family set for the next few centuries. And a lot of headache on managing the next personal island.
But why? It's a lot of quality of life left on the table.