> Some of the most free and wealthy (in terms of purchasing power) people I know do this. Compare the person who can't pay all the bills with $20k a month (a figure I recently heard from a real person!) with my friend also living in this town who is extremely frugal who spends $1000 a month and built up $40k in savings from a job.

Those two extremes both sound very unappealing. The obviously superior middle ground would be to make $20k/month and spend $5k, which would allow you to both save massively AND live very comfortably without pinching pennies.