I don't know who you are around that would rather be the homeless person with multiple Phds.

Well, that's not something I recall claiming. I concur that most people would prefer to live a comfortable or at least tolerable life instead of being homeless, to a degree that would override a lot of other considerations including obtaining a degree. I've dropped out of college to work a job personally, so I definitely see this.

As to preferring to be very rich instead of having a degree, a big part of the charm of being rich is that you can then afford to get a degree. Most people who are rich seem to get degrees. It boosts their social standing among other rich people and lets them select more fulfilling careers.

I also think people do sometimes prefer status over money, hence the oversaturation of the fiction market, and why people often pursue humanities/liberal arts degrees instead of profitable ones like STEM or business. The "starving artist" sterotype exemplifies this.