With all due respect, your own description puts me in the “wait” column.
“My son will have a baseline investment income and can work full or part time as the family needs. He is disorganized and would do well yoked. She seems to enjoy his eccentricities.”
Until a kid comes along, then the enjoyable eccentricities aren’t so cute anymore. This is a young guy who is disorganized, maybe we’ll work, maybe he won’t. His wife will have a job and he’ll at least have passive income.
Prediction: if they marry now, she’s banging her boss or another senior coworker within five years, somebody who makes things happen.
Get the young man up on his feet, out the door, self-sufficient, self-confident.
He is on his feet, works sixty hours a week and is independent. All his toys are paid for and he owns a truck and is saving a downpayment for a house.
I disagree. When my husband and I married, he was ‘disorganized’ and not a self starter. That changed as he saw the need to be more responsible. I was always aggressive in the workplace and I never cheated. I loved that my husband was the one who kept me from burning out.