Obediah2 Overton (apparently John1) was born before 1745 in order for his son, Willis, Sr., to be older than the Willis Overton, Jr., who married in 1788 at, presumably, twenty-one or more years of age. Family tradition holds that Obediah's first wife was Frances [-?-].35 Positive confirmation of this has not been found; however, the 1782 personal-property tax list of Orange County enigmatically lists "Overton, Obadiah, Fanny"-implying that Obediah was being assessed for personal property owned by a wife of that name. On 31 January 1788 in Culpeper County, to which he had removed, Obediah married Ellender Crow.36 The last record found of him is his personal-property tax assessment of 1817 in Orange County; no estate record is on file. The widowed Ellender last appears on record in 1824.37
Obediah, like his proposed brother George, surfaced in Orange County in the 1770s; both were in their mid-to-late twenties. Three years before George and Obediah affixed their signature to the legislative petition to divide Orange, Obediah made his first appearance of record. On 14 August 1774, he witnessed a deed there between Alexander Spotswood and Aaron Denny.38
As with most of this family, the young Obediah is best tracked through tax rolls. From the inception of the state-level rolls in 1782, he is regularly assessed for personal items through 1785 in Orange. By 1787 he had relocated in Culpeper, where one Francis Madison (an apparent employer) was charged with his tithe that year. Through 1791, he paid his own assessment in Culpeper but drops from the roll in 1792-the year that a portion of that county was cut away to create Madison. With the first extant roll for Madison, dated 1793, Obediah can again be tracked through 1801; from there he returned to Orange, whose rolls carry him through 1817.
https://www.wikitree.com/wiki/Overton-1823
