There is an interesting court case in the book, "Making Race in the Courtroom, The Legal Construction of Three Races in Early New Orleans," by Kenneth R. Aslakson.

June Oxendine of Bladen County, North Carolina, (present-day Robeson), had a daughter Charity Oxendine who had two illegitimate children who were bound out as apprentices, Since Charity was serving an apprenticeship when she had the children, she had to serve additional time to compensate her master for the "trouble of his house" during her pregnancy. (This was normal procedure for all women serving an indenture).
However, her master sold her and her children's time to one Thomas Ingles who made off with them to Mississippi where he held them all as slaves.
They managed to sue for and win their freedom in 1809 and 1812.

Meanwhile, most Oxendine heads of family in the Robeson County area were landowners.

So, like the Gibson and Evans families, there was a very obvious disparity between how free men of color and free women of color fared in the colonial and early national period.
Paul