In the Valentine Papers, Vol. III, page 1065, It states that John Pleasants witnesses the will of Robert Woodson, June 1, 1670. Byrd Title Book, p. 61.
Who is this Robert? In the will of John Woodson II, proved in 1684 he names his son Robert, his brother Roberts four youngest children, one being Robert. So that is all the Roberts' accounted for during that period.
I have different ideas but nothing of proof.
Maybe this was a will written by the first Robert and recorded on that day.
Why did John II leave part of his estate to his brothers' children if their father was still alive? Was their maybe another generation?
Was the Frances(usually female spelling) Woodson at Warwick Squeak maybe a son of John and Sara or maybe a daughter-in-law.
We know by a disposition that Robert gave in 1680, that he was born in 1634, so he was born 25 years after they came to Virginia. If they were children of John and Sara there might have been other children before John and Robert, or they could have been grandchildren.
Since the first John and first Roberts will is lost along with other valuable leads, other than a date on this we have no other information to help us if we do I haven't found anything yet.
Another needle in a haystack, if you have any ideas or proof lets hear it and see if we can figure this out.