Whew! too many James DORRELLs and Caleb SIPPLES! I agree with you that the first Caleb (c. <1725 - <1762 did indeed have a son Caleb (b. 1750-d. 1822). He was the one who originally married Alice (Celia) Walker, then married Elishe (Eliza) Laws, then married Mrs.Jane McClyment DORRELL who was the executor of his estate (with a wittness James M.c. Dorrell). This Caleb and wife #1 Alice also had a son named Caleb born in 1782, but since the Mary Dorrell/Caleb Sipple were admin of James DORRELL estate in 1781, that could not be their son born in 1782. I originally thought that Mary DORRELL and Caleb SIPPLE were related because he married Mary's daughter in law (your #2)in 1809 after Jane's husband James died in 1806. But then that doesn't make sense because the will was probated in 1781 and they did not marry until 1809!
Sure is confusing! Thanks.
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