Hello, I did a quick check in some of my Grayson Co. references, but didn't find your William Cheshire. However, I did find the following in on-line Grayson records:
1794 Grayson Co. Personal Property Tax:
Cheshire, William 1 Tithe (W,M, over age 16) with 2
1800 Grayson Co., Personal Property Tax:
Chessue, William 1 Tithe (W, M, over age 21)
1805 Grayson Co., Personal Property Tax List:
Chesher, John 1 Tithe (W,M, over age 16, no horses
I didn't find any more listings on latter tax listings in Grayson. I did check the land tax list and found no Cheshires, Chessue, etc., so he probably was not a land owner and was not listed in the free landowners pre-1800 Grayson list. Interestly, in one of the early personal property tax list, William was listed just before a Nathan Cox. Since he married a Cox, I thought Nathan could be related to Rebecca. So far, I found no marriage bond for Cheshire-Cox, but not all marriage bonds of early 1800's are available, especially on-line. According to the Grayson Co. Historical Society, many court and county records are missing from the years 1794-1806. So that time period is pretty sketchy.
I hope this helps a little bit. You may already have the info, but thought I would pass it along. I have a few brick walls in my family research and hopefully someone will be able to help fill in the blanks. Good luck, Linda
P.S. You might try tracing the counties from Grayson to Ky where they ended up after leaving Grayson and checking those county records.
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