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"He wants to enjoy the money now vs later. In addition, I think he believes he'll be bored without a job."

You might want to look at the "retired fools" board. There seem to be
quite a few discussions about retirement whats and hows over the
life of the board.

From my perspective, the dollar issues require predicting the future.
I am terrible at that sort of thing. Most of the suggested readings
on retirement suggest expecting 4% withdrawal as a "safe" approach.
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