I'll tell you what I don't fantasize about.

Not knowing who you're real friends are. Being objectified by everyone you meet. Having people judge you just because you have wealth... And god help you if you inherited any part of your money, because fuck the fact that you took some and made it a hundred times more, no you're a silver-spoon brat, and no personal financial achievement counts. Having to hang out with other rich folks, or pretending you're not wealthy to get along with middle-class and lower people. Having people get offended because you don't want to lend them cash, even though you don't do it because you don't want to fuck up the relationship. Not being able to complain about anything cause hey! you're rich! what the fuck do you know about problems?! Well, guess what... my problems can't just be solved with money. Having people constantly trying to spring their "investment opportunity" on you, and when they aren't shitty ideas, they're outright scams. Which brings us to constantly looking out for people who want to hustle you, who justify it because you're rich and "don't deserve" it. Not knowing if that chick is attracted to you or your wallet, and when you hide your wealth, seeing their eyes light up green when they find out. Having to make sure you're not surrounded by yes-men. Having the people who you've helped make money shit on you once they "get theirs" and their character changes, because they don't have a use for you anymore. Reaching the point where you know you're business ventures are doing damage to something, somewhere, and trying to find out where you'll do the least amount of damage and failing at that. Realizing that no matter what you buy, no matter how much you make, at some point you'll get sick of trying to fill the Pythagorean hollow. Knowing that no matter how fair you'll try to be, your loved ones will bicker over your shit when you die, and it might tear them apart. When you fail, and if you fall, the only ones not applauding your downfall are those that are financially dependent on you, but they will blame you.