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I'm glad you got to see your friend before he passed, wring. He sounds like he was a fun guy.
Not a solution, but a data point on enabled offspring: I had an uncle who was, shall we say, overly financially reliant on his mother well into his late 40s when Grandma died and the gravy train dried up. I wondered what would happen when she wasn't around to prop him up anymore. Turns out he has managed adequately for 20yrs.
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