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two of the trust fund friends I know are miserable, the other is doing okay but still struggles.
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yea 80/20 - most trust funders I know are unhappy. Another parallel might be the kids of celebrities.
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Another interesting behavior of trust fund kids is that they fiercely try to maintain and guard status (status seeking monkeys). In a post-scarcity world -- status becomes all the things you alluded to: leadership, charisma, charm, etc.
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tldr No. The world would be like Star Trek.
I don't think so. A fair bit of the trust fund kids that I've known are pretty unhappy. If I had to guess, they're unhappy because society uses wealth as a proxy for worth. While their wealth and perceived worth are high, it has nothing to do with them.
Humans measure things against other things, and we measure ourselves against other people. Trust fund kids have fewer examples to measure themselves against, so unless they carefully select samples, they probably have a hard time gauging their worth.
In a post-scarcity society, post-scarcity is common and we'll cease measuring our worth using wealth as a proxy. I'd guess we'll measure worth by politics, leadership, charisma, charm, intelligence, and physical attractiveness. If you found a properly isolated clade of trust fund kids, I'd guess they measure worth on dimensions like those.