Beautiful woman and wealthy men is older than the hills. It’s not just good looks, a la Clooney, it’s “the look,” i.e., piercings, tattoos, etc. “Edgy.”
Some women will be attracted to a homely man with the ‘bad boy look’ more quickly than to a handsome, solid/sober/responsible guy.
You may have just described why I enjoyed so much success in the dating world. It's been over 21 years now, and I still miss dating.