Two thoughts: Skill levels vs income over time: I left the 'employment' world 20 years ago to farm and I was at 50,000/year. If I were to seek a regular job at my skill level, to keep up with inflation of costs, I would have to ask over 100k, but nobody will pay that much for a technician without a degree. This staggering jump for deflation of employment value isn't obvious if one doesn't leave the system and try to come back. I know a lot of people who have been trapped in the past wages (less than 20/hr) all of their working lives. You used Naples Florida as an example. Most of Florida is more like the Pottersvilles of Orlando and Tampa.
Second: the work you've done here is good. Thanks. I would classify the step between upper middle and wealthy more subjectively: Those who have to work to eat vs those who never will. It then becomes a shift from employment to passive income only. Some still seek power or glory through work, but the key is that they don't have to, and these are the donors to politicians.