As an aside, I'm curious what would happen if a slave owner went to jail and there was no one to run their estate. Obviously this would probably depend on the size and wealth of the estate too.

In colonial New York City there were issues with enslaved people who formed criminal gangs, which some scholars believe may have been adaptations of west African secret societies. These groups appeared to have been based at john hughson's tavern located where the World Trade Center is now located and became the scapegoat for a series of fires that threatened NYC in 1741. Ultimately over forty people were executed in a gruesome series of public burnings and tortures. It was only when the skilled slaves of prominent New Yorkers were implicated that this witch hunt ended. At that point, slaveholders were not compensated for their lost human properties but in the 19th century slave states like Maryland and Virginia created statutes to compensate slaveholders for human property that was executed. Sources: New York burning by Jill lepore, slavery in New York by the new-York historical society, NYC African burial ground history report