Forgive me, it’s another post on r/askhistorians about Hamilton. I did try to do a search, but did not find anything really related to this question.
Alexander Hamilton was a bastard son of a prostitute, while Elizabeth Schuyler was the daughter of a wealthy political type. However, from what I’ve read (and it’s not a lot) they seem to have had a short courtship followed by an engagement readily consented to by Elizabeth’s father. My understanding of 18th century societal norms are admittedly pretty colored by Jane Austen novels, however, I’m curious to know if Hamilton’s background/parentage would have been a concern for Philip Schuyler. Would this engagement have raised eyebrows? Or was Hamilton’s position as an aide to Washington enough to ignore his origins?
This doesn't address your broader question, but I want to point out that as far as I know, Rachel Faucette, Hamilton's mother, was not a prostitute. She was briefly imprisoned in 1749 for allegedly cheating on her husband, John Michael Lavien, with mapmaker Johan Jacob Cronenberg. Court records stated that "agents of the court . . . seized [Rachel and Cronenberg] in their bedroom, undressed and with more debauched circumstances that sufficiently demonstrated their shameless intercourse and scandalous life."
After being released from prison, she didn't return to her husband, but instead went to St. Kitts and, without divorcing her husband, began a new relationship with a James Hamilton, the probable father of her two children, James Jr. and Alexander.
In 1759 Lavien filed for divorce, claiming that Faucette had "given herself up to whoring with everyone", that she had "begotten several illegitimate children", and that she had "shown herself to be shameless, rude and ungodly." He denied that either of Faucette's children were his, and said that her "whore-children" shouldn't be permitted to inherit "what such a legitimate child alone is due." The court found in his favour, granting him divorce and stating that "Rachael Lewin’s illegitimate children are forfeited all rights or pretensions to the plaintiff’s possessions and means."
When Lavien referred to Rachel as a whore, he meant that she was a promiscuous woman, not that she exchanged sex for money.