I don't know how DT will end. (My guess is rich and largely unbothered.)

But I agree with your perspective that he did not "have to" live by the average person's standards, and therefore has limited understanding of reality and what it is for most people. Of course, he is the star of his own show in every enterprise he starts, and there have been no regulations or evaluations of his work, and that is why he is so unaccustomed to being assessed or questioned, and so offended by statements about his decisions, priorities, spending and affiliations. Culturally, his presidency was a lesson in what happens to people who rarely have to fight for anything, can keep tooting their own horn, never have to grow up morally or emotionally, and how much support and reward is available for just that!

A life without consequences - that is what he embodies.