Re: Cunningham Sample
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If Ann Cowan was born 1755, then it is unlikely that a son named John would be in the 1790 census (assuming marriage at no age before 16 (1771) and a child the next year (1772).
The judge John Sample (b. 1770s) of Butler Co., OH and Randolph Co., IN (and prob. also of Washington Co., PA) also married a Taylor, this one named Anne.
The connection of both my Driver and your Sample family to York Co., PA are suggestive for John Driver m. Catharine Sample (sister of judge John above), but I don't see the connection yet.