I regret not being able to go to any of the Fountain Valley Fry's midnight releases that were hosted by the Blizzard dev teams. I wasn't even in high school yet when those were still being held. In hindsight, I think my mom would have been willing to take me to one if I had asked. It was a ten minute drive from home.
I was really sad when that Fry's closed down. Nearly all of my PC gaming purchases came from there and the ACP Swapmeet up until 2006 or so, when I switched to Steam, so it felt like losing a part of my childhood. I haven't visited the location in a while, but I'm assuming it is still empty and fenced off.
The first dinner I ever ate after arriving in SF was at their original HQ's cafe/restaurant, thanks to some friends who worked there. It was so good! I regret not having gone as a guest more often.
Granular progressive taxation is the best answer to your question.
Trying to define buckets with arbitrary thresholds is futile.
It greatly benefits the top outliers, since the top bucket will have a huge disparity between its strictly defined lower bounds, and an infinite upper bound.
There's no need to "define rich". A formula without defined bounds (this is the most important part) should determine how much tax you pay, and it shouldn't discriminate between different forms of income. More importantly, all net worth gains should be taxed equally.