what you are looking at, my dear, is mere fantasy. a man who is rich and handsome would not stoop down their status so low as to not marry someone beautiful. the woman, by all means, does not have to be rich. she just has to be beautiful. beauty takes a woman farther than anything.
actually, i take that back. she just has to be alluring. cleopatra, the greatest seductress, wasn't beautiful but she was alluring and that's how she's attracted kings. so, if your looks aren't all that, you need allure. attraction in men is mostly physical and that's a fact. education, being sweet, honesty, loyalty, and kindness play only minor roles. it's a tough pill to swallow.
but, your scenario is indeed possible by all means. it probably takes a creative and intuitive mind but it can be done.