Regarding What are the dates involued?
I'm a descendent of Thomas Bowles through his daughter Maria W. Bowles (who married John Pate). This comes from the 1836 Will of John Williamson of Henrico County, VA. In this Will, John Williamson refers to Thomas Bowles as the widower of his [Williamson's] daughter Rebecca Williamson. He also mentions Thomas and Rebecca's children: John Williamson Bowles, Maria P. - wife of John Pate, Betsey - wife of William Davis of Orange Co, VA, Lyddall Boyles - a minor, and Maria Ann Bowles - a minor.
Additionally, there is a record of a marriage bond being issued for this marriage between Thomas Bowles of Hanover County to Rebecca Williamson, daughter of John Williamson, on 21 Sept. 1803 (from "Marriage Bonds of Henrico County, VA 1782-1853", by Michael E. Pollock, Geneal. Pub. Co., Baltimore, 1984)
Maria W. Bowles, wife of John Pate, was born about 1806 (1850 and 1860 census) and died in 1866 (probate records). The Pate's owned a "plantation" immediately south-west of Old Church in Hanover County, VA. John Pate died circa 1848.
Is this the same Thomas Bowles you refer to as William's brother and as a son of Deborah? Or do you know how they might oterwise be related?