You stated in this post "William Roper is listed in the 1790 Caswell County Census." While it is true that William ROPER is list in an extant Tax List for Caswell County, NC, in 1790, the Census for the part of the county where this William ROPER resided has been LOST. There is NO EXTANT CENSUS DATA for this William ROPER in 1790 and he has NOT yet been identified in any subsequent Census.
You also stated "Died sometime after 1795 in Caswell County, NC."
You further stated "He was born sometime before Mar 24, 1727." What is the basis for your belief that David ROPER was born before 24 Mar 1727?
At least one of David ROPER's sons seems to have been born bef 1756. David ROPER is shown on Orange County deeds beginning in 1760. It seems likely that this David ROPER was born before 1736. There is essentially NO EVIDENCE linking this David ROPER to New Kent.
It is my understanding that William ROPER was listed in a 1786 Tax List for Caswell County, NC. This would seem to support an implied year of birth of before 1766. If there is any other data which supports a more specific date range, it is UNKNOWN TO ME.
The earlier end of the date range would seem to be constrained by the date of birth of William ROPER's father, David ROPER, however the precise David ROPER has NOT been established and the precise year of birth is reasonably well established for only one of three David ROPERs who seem to have resided or owned land in Caswell, NC.
What is the basis for your belief that David ROPER was still living in 1795? Also, what is the basis for your belief that this David ROPER died in Caswell County, NC?