The first record I have found of James in Halifax County was in July of 1766:
Halifax County, Virginia Court Orders, 1764-1766 (Plea Book No. 5, Part 1), Pub. by TLC Genealogy; p. 118:
July Court 1766
Robert Chandler is appointed Surveyor of the Road from Marrowbone Cr to Smiths River, and it is ordered that he, with Elisha Harbour and his male laboring tithables, Elijah Harbour, Francis Kingston, Jessee Langston, Richard Whitt, Preston Kendrick, [Blank first name] Cockram, Edward Cockram, John Gillaspie, William Edwards, Thomas Edwards, Thomas Edwards Jr., [Blank first name] Mays, James Edwards, William Rice, James Elkins, William Sams, John Sams, James Bolling, George Daniel, Charles Burns, John Bolling, John Ray[Rea], Merry Webb, Martin Webb, James Wilson, and William Dagg, do forthwith clear and keep sd Road in repair.
I believe this to be our James Wilson since this is the same area he later had surveyed (Smith River) and some of the men listed contained in other documents where James appears (such as a deed with witnesses and/or adjacent land) and thus know to be his neighbors (e.g. Webbs, Bolling).
Note: This portion of Halifax County became Pittsylvania County in 1767, and then Henry County in 1776. James could have lived in the same location yet be located in three different counties in the space of 10 years.
The Halifax County poll lists (which were effectively the House of Burgess election results) did not include James up through July of 1765. Unfortunately, there is a gap in my source from that date until December, 1768, at which point James would no longer be living in Halifax County (due to the formation of Pittsylvania). There were two or more Thomas Wilsons in these lists, however, but I think it is unlikely that any of them would be James’ son as I know there were Thomas Wilsons in the eastern part of Halifax (not in James’ neighborhood), and there continue to be possibly the same Thomas’ in later years’ poll lists when the Smith River area where James lived was no longer in Halifax. Plus, there was no mention of James other son Moses in the pre-1766 Halifax poll lists either (although it is possible that he was not of age yet).
James possibly moving to Halifax sometime after July 1765, is consistent with the theory that he moved from Prince William County, since a James Wilson with 4 tithables (himself, 2 sons and son-in-law?) were in PW in 1765 and did not own any land at that time.
James next appears in the first Pittsylvania tax list in 1767 with his son Moses. Thomas also appears in this list.
Later surveys of land were made for Thomas on April of 1768 and James, Thomas and Moses in February of 1768.
I don’t know any of these gentlemen actually lived on the land prior to the survey, nor how they acquired the land. The survey was part of the deeding process, but it initial acquisition of the land could through various means. There are no deed transfers that I can find for these parcels (except for possibly later transfers).