Michael,
 
A note of interest.  I saw a posting in your webite about Reuben Cooley from Jessamine Co, and am now certain that the Reuben Cooley who died in Jessamine County abt 1795 was Thadeus Cooley's eldest son.  I have tax lists from Wythe Co, VA, which show Reuben living with Thadeus in Wythe Co in 1787, which place his birth around 1769.  Reuben is also listed as a witness to a will in Wythe Co in 1792.  Then he dissapears from VA records.  He is reported to have married Mary Polly Martin abt 1793, and they had Reuben Jr in 1794 in Kentucky, shortly before Reuben Sr died.  Those Cooleys have remained in Jessamine Co, KY for generations, or nearby in KY.  Thadeus had a daughter named Matilda, named in his 1814 will as Matilda Stuart.  Thadeus' son John, my line, had a wife named Martha Snodgrass.  Her brother John Snodgrass married a Matilda Stuart in Wythe Co in 1818 - took me awhile to realize that this was Matilda Cooley who was married previously to a Stuart, and was Thadeus' youngest daughter.  Mary Martin's father Benjamin moved to Jessamine County, KY by 1810.  He was from Orange Co, VA - not far from Wythe Co.  Mary remarried in Jessamine Co in 1801.  Reuben Cooley Jr remained in Jessamine Co.
 
Now it all fits together.  Reuben moved from Wythe Co, VA to Jessamine, KY abt 1793, where they had son Reuben Jr.  His wife Mary remarried Stephen Walters in 1801 and remained in Jessamine KY.  John Snograss and Matilda Cooley moved to Jessamine, KY bet 1818 and 1820, likely to be near their nephew Reuben.  VA Tax lists show that John Cooley left Wythe Co abt 1822-23, and must have arrived in Fayette Co, IN by 1824.  The Cooleys likley met the Snodgrass' in Jessamine, KY c1823 and traveled together to Fayette, IN, where John Snodgrass died bef 1834.  The Cooleys traveled along one of the famous pioneer routes, from Wythe, VA across mtns thru Cumberland Gap into Kentucky.  John Cooley and Martha Snodgrass took John Snodgrass' daughter Margaret into their home after John died, and Margaret was named in John Cooley's Last Will dated 1845 in La Porte Co, IN. 
 
Regards
 
John