It's like winning the lottery, you're like "great!", you quit your job, and go sip cocktail and f*** high-end escorts day in day out on some paradise island. That will get old after a few weeks, and you'll start longing the days when your life had some challenges built into it.
I also think that you never get a virtue without a corresponding vice. If you're very good-looking, how do you know if people truly appreciate you or if they're just being sycophants who will tell you everything you want to hear so they can keep you around? This has more downsides than people like to think.
My ex-girlfriend would always do everything I told her to do because she didn't want to upset me. You'd think "great, my personal slave!", but people actually hate to do things they know they don't want do, and deep down, they'll become resentful about it, even if it's unconscious, and their frustration accumulates over time.
I've gotten the old "world's smallest violin" treatment for writing about this in the past (and that's not a dig at anyone, it's completely understandable really).
The happiest people in life aren't happy at all, they're humbly content, because they don't constantly have their mind on this pursuit of eternal happiness. They know that Utopia isn't ever going to be out there, and life has to be set up with some form of balance between excitement of success, and the difficulties of failure.
Only when forced out of your comfort zone are you really going to gain any sort of self-realization as to the extent of what you can achieve, or even just feel. If everything is eternal bliss and you gorge yourself on all of the superficial things that you've been brainwashed into believing are happiness, you'll quickly be unchallenged, and empty.
There's a huge amount of terribly depressing stories of lottery winners, to go with your example. Most people are completely out of touch with themselves and don't understand their own psychology, and this couldn't be explored more than a person with an unimaginable amount of money just falling on their lap (especially if they're relatively young, but definitely not exclusively).
Challenges, achievements, disappointments are also now unimaginable, once that money hits the bank account what is expected is never ending blissful gluttony. That's just impossible to attain forever.
Even the thrills get dull inevitably, and seeking more just ends in catastrophe.
A woman I know in her mid-30s, very attractive and a wild previous life of drug use and probably Chad's, put this simply and brilliantly when this topic of a 25 year old local winning big in the lottery and how amazing that is to be so young and have the world as your oyster, imagine that?!
"Oh, no! God no! If I won the lottery 10 years ago I'd be dead."