I do not dream of being rich.
These are the kinds of things that I would define as real luxury. And they are definitely tempting.
Adnan Khashoggi traveled on a private jet, always accompanied by a chef, masseur, and chiropractor.
And he sold arms that found their way into the hands of child soldiers.
And a valet.
And a barber.
He may very well have been a soulless, heartless monster, but he looked … fabulous.
Then there was Nubar Gulbenkian. He, like his father before him, used his wealth for good. But he was remembered for being described: “Nubar is so tough that every day he tires out three stockbrokers, three horses and three women”.
Meanwhile, Charles Feeney made billions after founding a chain of duty-free shops and spent the rest of his life giving the money away, mostly secretly. The Wikipedia article says his philanthropy funded a thousand buildings all over the world, none with his name on them.
All I want is enough to buy this island and have sufficient funds for transport, supply and security.
I think that often rich people (at least rich people who don’t regularly have to deal with money) don’t actually know or comprehend how much things cost. Case in point, your example of paying for airfare, hotel, and spending money for 30 people to go to Spain and then balking at the cost of the breakfast buffet.
My wife and I do pretty well financially, but I wouldn’t mind being a lot richer. Probably not obscenely rich like the Roy family from Succession. But maybe rich enough such that I didn’t have to depend on a high paying corporate job for most of my income.
He also once signed a fake rebate check for 25¢ that had been sent to him by Spy magazine in a prank. (The checks were real, but the stories behind them were fake.) In the early 1990s, Spy sent pitifully small rebate checks to filthy rich people, and followed up with smaller ones if they responded.
Khashoggi tied with another guy for the lowest-value check that a billionaire would sign. The other guy was a Queens-born casino operator who was having money problems.
You forgot to mention his 86 metre yatch Nabila, which was bought by the Quees-born casino operator just mentioned and became the Trump Princess. Beautiful guided plumage. Men of taste flock together.
I read that Spy article when it came out. It was obvious to me then that they had nothing to do with those checks. It was one of their accountants
But isn’t that them? The thing that drives me nuts about the portrayals of wealth like Succession is that even better than the money to do lots of things, they’ve got the money to do nothing. There never seems to be one character that just chills in a nice house reading the classics or something. No one knows how to be rich.
Being rich would definitely make my dreams come true, but I wouldn’t say I dream about it, anymore. I’m too jaded for it.
I could and would put untold millions into nature preservation, even just staying local. Loss of habitat is a tremendous threat to life and it happens before my very eyes. It would give me immense and sustainable satisfaction, something that luxury cars or outrageous trips abroad couldn’t.
Having someone else make me tasty, healthy and quasi-infinitely varied meals the year round would be a huge boon, most importantly by increasing the time / energy I have to do other things. Even living in the city, the food quest is a drain on varied resources.
I haven’t been sick for realz, but if / when that happens, being rich would make a world of difference.
Sure, I idly think about it especially when the news is a reporting a billion dollar jackpot. My idea of “being rich” is pretty much the same as me now except without needing to work and with nicer stuff and knowing that my family is taken care of – not flying a solid gold jet to my private island (also made of gold). I guess that’s why I wouldn’t really give a shit about “rich people problems” either. I don’t want to talk to people now; I’m not going to suddenly start giving a shit about high society when I have my billion dollars (less tax).
I have a somewhat insane fantasy about spending millions on my very modest house, turning it into a fabulous castle on a tiny suburban plot. Something like what Ned did when he spruced up the ol’ Flanders place with the monkey’s paw.
I have this dream of having a concert grand piano in the living room, even though I can’t play one. I think what I really dream of is having enough space for a piano. Realistically, I’d rather have a big game room with a pool table, pinball table and stand-up arcade video games and perhaps a dedicated home theater.
There will always be moochers, but I think most people feel like they need to be doing something productive, no matter how much money they have. Which is why you will see some unhappy retirees until they get into something like volunteering or other projects. I think if I were a billionaire I would still want to work, like 20 hours a week. But I would be working on what I wanted to work on - in my case, writing books, and paying other people to market them.
You wear your underclothes twice?
And when they get dirty you turn them inside out and start anew, and then front to back after a week, what else?
Except you are a superhero, in which case you wear them over your tight fitting pants. In this case, it is the pants you have to turn inside out, then front to back after a week.
OK, I’m gone 
The list of people letting me wear their underclothes – once, twice or otherwise – is not all that long and definitely not terribly distinguished.