Years ago (80's ?) Oprah had a show on lottery winners who were unhappy/had lost all the money. Some were saying how much happier they were before they hit it big on the lottery. The audience didn't buy it. Oprah then said something that stuck with me:
Money may not buy happiness but it can eliminate a lot of things that make you unhappy.
I would have a lot more money if I'd stayed working for 10 more years or more. But I'm plenty happy with what I have. (Which is much less than many here). Not going to work makes me happy.
Every once in awhile, I'll come across those "lottery curse" stories, of people who have won the lottery, but end up being worse off because of it. They're good at scaring people, and generating mouse clicks, I'm sure. Of course, you never see stories about those who have won big on the lottery, and lived happily ever after.
I have a feeling that lottery winners might be a bit skewed, though. People who play the lottery tend to be poorer, not have the best math skills, how much it truly costs to live "rich", etc. As a result, the rags-to-riches-to-rags stories might be fairly common. But, overall, I imagine the majority of winners still learn how to handle it.
Some relatives of mine won $100,000 back in the late 1980s or early 1990s. However, they were serious gamblers, and liked to put on airs. They lost a single family home in the 1990s, and then a townhouse in the early 2000s. Towards the end, the husband had gotten really sick, and they ended up getting divorced, for financial reasons. I think he was able to get Medicaid or some other kind of assistance going that route. But the wife ended up moving into an in-law suite that my Grandmom's cousin had. And now lives in a trailer in Florida, that was recently damaged by a hurricane.
As for the whole "more money vs more work" conundrum, I'm sort of on the threshold of that right now. I tend to think of the old "BS Bucket" analogy, where eventually no amount of money will offset the amount of BS at work, and then I know it's time to go. Only problem for me is, the BS has actually gone down. I'm reasonably happy right now, as things are. I only go into the office one day per week, and they're pretty flexible with my overall hours, as long as the work gets done, and as long as it totals out to 80 hours every two weeks (can be a combination of actual work hours and PTO/holiday hours). So at this point, I don't know that I'd be any happier retired. Of course, that's subject to change!