This is such a good idea, I am so glad I saw the Geneabloggers post about it on Twitter this morning. I have thought about doing this for a very long time and was not sure where or how to start.
So I pulled out some wills and here is what I found this morning..more another time.
William Carrow who dies before March in 1823 in Murderkill Hundred Kent County Delaware,in the last census I find him in, indicates that there are three "all other free persons" living in his household.
However the inventory lists "1 Black Boy Coled Daniel ", " Ditto Called Jamiz" and " 1 Black girl Patty" at a total of $290 .00. That being said however John Craig mortgaged 1 Black man for ten years $100 and paying $60. This either means that Daniel was really only indentured or that he ( John Craig) had 10 years to pay the other $100.
My own ancestor William Keys upon his death in October 1796, Dover Hundred, Kent County lists a Negro man Richard valued at 30 pds. and a Negro woman Misery valued at 37. William Keys had originally lived in Queen Anne MD but came back from the Revolutionary War in 1783 and raised a family in Delaware. By 1797 no slaves could be sold out of state from the state of Delaware so it is unclear what might have happened to Richard and Misery.
In Dorchester County MD as well as Kent County Delaware between 1800 and 1820 there were free families of color with both surnames found on the census. William Carrow living in the Vienna District of Dorchester County had 5 family members, was a free person of color and apparently also owned slaves.
I am not sure whether any of these named in these two wills had terms to their servitude or not.