Hi,
My interest in the Kimsey is peripheral, and secondary to a Cunningham project I am working on. As you know, Benjamin Kimsey's brother William of Lost River in Hampshire/Hardy Co., WV married Elizabeth Cunningham.
As a coincidence, most of my ancestors came from Pendleton Co., WV, which is adjacent Rockingham Co., VA. I have researched most Pendleton families for over 30 years, even the ones I'm not related to. Arthur Johnson Sr.'s wife was Margaret Phares, a dau. of John Phares who came to Rockingham from near Philadelphia.
Soon after Arthur Johnson's death, his widow remarried to William Gregg/Gragg Sr. Around 1770, they moved to the Seneca Rocks area in current Pendleton Co., WV. Margaret died there by 1790. William Gragg Sr. remarried to Martha Wheaton in 1791, and she was his widow when he died in 1794-5. You can read about this on-line in an article a friend of mine, Warren Skidmore, wrote about the Phares family. Google those key words and you will find the article.
There is some circumstantial evidence that William Gragg Sr. may have had a brother named Robert, i.e. same generation, same locale. It's not too far-fetched to me to think there may have been a sister around as well. This could be your Margaret Gragg who m. Benjamin Kimsey Sr. Kimsey was in the Brock's Gap settlement, not more than about 5-10 miles from where the Graggs were.
Just some food for thought.