I think there is adequate documentation to support the connection.
I have John & Margaret being married in Virginia after 1742.
I have not been able to pinpoint a specific marriage location but John's parents came from around the Middlesex County, VA area. Several of John's children were born in Washington County, MD. There is documentation mentioning the Rappahannock River. This area would be south of Washington County, Md (about 50 miles). Additional documentation references several of the South family being born in the Hagerstown, MD (Washington Co) area. There are also references that Bedford Co, Virginia may have been residence to some of the South families. Bedford County, VA is southwest of Hagerstown, MD and would be a natural route that led to the Cumberland gap. No doubt this is the route many of the South families followed to reach Kentucky.
John is found in the 1760's in Bedford Co, VA. In 1778 he was in the command of the Boonsboro militia. Most if not all of his children were born before reaching Kentucky.
Hope this helps,
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