I don't know that there is some objective "right" level for everyone. It's all subjective and very, very personal. Taylor Swift's life would make me absolutely miserable, because I am a very different person with very different needs. And yet MMM's life would also not make me happy for the same reason. And both of them would probably hate my life with an equal passion.
I go back to that "two levels above/below" thing that I can't ever remember the name of. I am anchored around where I am now. I can easily answer for $1M or $10M because they're within my range of understanding. I cannot possibly answer for $100M or $1B, because that is so far beyond my own experience that I have no idea how I'd actually feel/think. And yet the people who have $100M or $1B aren't exactly giving it all away because they're miserable and want to have less and be happier. So I think for someone with say $1B, it's not about the money per se, it's about doing the thing that brings in that money -- it's some driver to achieve or create or whatever, and the money comes along with it.
I do think that different levels of money bring different kinds of problems, and that the people most likely to get in trouble are those who suddenly change status without the knowledge/experience/guidance to handle that successfully -- particularly if you think having more money solves all your problems and thus are completely unprepared to face the "mo money" problems when they do happen. I remember when DD was small and asking me to buy her things, and I'd always say, "no, we can't afford it"; then I realized that was not true. I was repeating the line I had heard my whole life, but we were much more well-off, so I needed to figure out how much is enough and how to raise kids when I had more money than I actually needed.
Now, that was a much better problem to have than my mom dealt with; she said no all the time because we truly couldn't afford it. And I sure as hell wasn't going to quit my job so I could re-create the poverty of my childhood, just so I didn't have to figure out how to handle DD's questions. But it was still a new issue that our greater wealth created, and I had to figure out how to manage that. And after 20+ years, I've figured out how to manage most of the issues that come along with the $1-to-$10M wealth range. But I still have no experience in the $100M or $1B range, so I have no idea what those issues actually would be.
For me, $10M is better than $1M, because of the freedom it brings. Like my mom was able to help my sister buy a house post-divorce so she didn't have to uproot the kids. And when my MIL had cancer and was prescribed a drug and Medicare was fussing about coverage, my FIL just plunked down $20K to get her started on the meds, without batting an eye. I like the idea of having a big pot of money that I never intend to touch but that is there for those unexpected things; again, going back to the whole growing-up-poor thing, knowing that I can solve a problem by throwing money at it gives me a tremendous sense of comfort and happiness, even when I don't choose to solve the problem that way.
OTOH, I wouldn't want $100M, if it meant that everyone knew who I was and how much I was worth. Which means I probably don't want it, period. I have a ridiculous pull to real estate; I visit somewhere and love it so much and want a home there. So if I had $100M, I'd be the person with like 8 homes. And if I was always out traveling and buying new homes, everyone would have a really good idea of how much I was worth, which we've established would make me unhappy. So better not to be tempted. ;-) OTOH, other people with different personalities seem to handle that just fine -- and like I said, they're not exactly giving their money away to reduce their wealth to my range because they're unhappy having so much. So I have to assume that from their perspective, $100M or $1B is better than $10M or $1M.
