To me it sounds like this woman isn't in to him as much as he is in to her. He sounds like a catch, but to someone else, because I don't see anything where this woman feels anything for him at all. She should give him back the ring and come clean to him and to herself.

Theres always somebody better, you'll always be settling, but from what I hear, ofvthe man is super wealthy, super fit, well groomed, taller, then he isn't staying with one woman more than likely, so there is this weird conundrum where nobody is ever happy

He sounds like a catch, everything every woman I have known in later life dreams of finding in a partner, to me she sounds like the silly girls I asked out at school and in college who would tell me I was just "too nice" to be boyfriend material, and then dated guys who knocked them up at 15 years old and headed for the hills, or beat the living shit out of them for expressing an opinion.
She'll learn, I hope, eventually

An example of an unprepared child launched in life.

The Dad does not seem to command respect and in spite of the Dad telling her what he thinks, she is asking for advice on social media. What did the family do for 20 years raising her? No wonder there is a crop of "expert therapists and counselors online'.

IMO, a child who is held in arms regularly since infancy, breastfed, read bedtime stories to, spent plenty of time with, worked with on homework, accompanied on various childhood events, functions, sports and most importantly - Not Left with Babysitters will grow up emotionally secure and healthy. A child should always come home from school to a loving mother and warm food, energized and ready to start and finish homework. Else they will be led by hormones and bad company in vulnerable years.

I have not seen such emotionally broken children in many other societies.

Do him a Huge flavor and do not marry him!!!!!!!
What a user!

Never settle. Wait for the right situation, or just be happy on your own. That would be my advice, having paid the price for settling in the past.