What do I think of his actions? Not much, actually. *shrug*
Being in their late 60s doesn’t make someone wise, 100% in control of their emotions, or any less “stupid” or “silly”. Neither do any of the financial examples you gave above. Would his behavior be more acceptable to you if he was 20...
This thread has been cleaned up and returned to the open forum. Past life remorse/guilt is complex and cannot be summed up in a one-sided joke.
Please stick to the OP’s experience and questions.