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What’s wrong with dying penniless? It’s not like you can take it with you.
It's the "dying because you're penniless" part people have trouble with.
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When people use "dying penniless", the "because you're" is implied outside of the specific context of someone who is not penniless discussing what inheritance they'll leave to their heirs.
Literally, the ONLY time I have ever heard it used in any other way, is when directly preceeded by "although wealthy, they dedicated the rest of their life trying to give away their fortune, and died penniless" and the implication is they were happy about that because they were trying to.
And that's happened what, like 6 times in human history? (hyperbole for mild comedic effect, pls no lectures)
I don't know how the other guy can see "died penniless" and think "good for them, can't take it with you!"
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Not everything in life and in comics is written out in full ¯\_(ツ)_/¯