I have given your note a lot of thought, especially in light of other research that has come to my attention.
Let me be sure of what you are saying and what I understand, because I got really lost about half way through your post.
1. Rebecca, daughter of Richard and Mary (Terry) Dudgeon, was married to John Dickerson. This is what I have come to conclude, as well, and let it be understood that I refer to John Dickerson, the younger, Junior, or whatever reference makes it clear we are talking about John Dickerson born 1747 or very nearly so, in Virginia.
2. I am understanding you to say that William Hill married Martha Dudgeon, and that Martha was a sister to Rebecca. He stood as security when Rebecca asked for letters of administration regarding the estate of John Dickerson.
I get confused when you mention John having a son not yet born when he made his 1776 will, and James not being a son.
John Dickerson, the elder, was born about 1719, and is my direct ancestor, for whom decent documentation exists to connect him to his children, and in particular his son, also named John, for whom even more documentation exists. The elder John Dickerson also had children Martin, Valentine, probably others. The three I mention all ended up in Fayette/Jessamine County, Ky.
James Dudgeon, of course, would not be a son, and that sort of threw me, but I may still be misunderstanding exactly what you meant. I am thinking that James was a nephew to Rebecca Dudgeon Dickerson and Mary Dudgeon Hill. James Dudgeon, born 1763, is a supposed son of Richard and Mary Terry Dudgeon, but I do not have any good proof about this.
The James Dudgeon who assisted Rebecca Dudgeon Dickerson so many years later in Jessamine County, KY, and became a guardian to her son Obadiah Dickerson, I believe may have been her nephew, but possibly her brother.
John Dickerson, the elder, made his will in 1776. We know that he died before June, 1788 in Halifax County, VA. John Dickerson, the younger, born 1747, married to Rebecca Dudgeon, died before 1789. Betsy Strader, whom I respect above all others in this line of inquiry, just has a gut feeling that the younger John Dickerson may have met his death shortly after getting news of his father's death, and possibly as he traveled from Jessamine County, KY, back to Halifax County, VA, to attend to the legalities .... and that may very well be why his wife, Rebecca Dudgeon Dickerson, applied for letters of administration.
Rebecca Dudgeon was an unusual and remarkable woman for her times. She insisted on using her maiden name during various court cases. She did remarry after John Dickerson disappeared, and after being listed on the tax rolls following his disappearance until his death/disappearance was accepted. She married a total jerk named James Bates, and after documented abuse from him, managed to obtain a divorce.
I have also seen many family novelists simply ascribe Rebecca Dudgeon as the wife of the elder John Dickerson because of something they found to be convenient on World Connect, which may be the biggest disservice to serious genealogy since the age of computers.
Anyhow, still a lot to unravel about these folks, but I hope I am understanding you correctly for the most part, and may have shed some light on some details.
I have come to agree with you, that the Rebecca Dudgeon we are discussing is a daughter of Richard and Mary (Terry) Dudgeon.
With much appreciation, and no excuse for the time it has taken me to think through my response,
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