Focussing on Leonard Sale in Logan and maybe Todd Counties --
I see that in his household in the 1810 census (online at Rootsweb) are TWO males in the 26-45 age bracket.So he's at least a little bit older than 25.Therefore he was born no later than 1784.(The other adult male could be a brother, or just a farmhand, so I'm not hazarding any guesses about him as a family member.)
I believe that the origins of this Leonard Sale of Kentucky go back to Caroline County, Va.The reason is that very close to Leonard on that 1810 census I noticed a Reuben Sanders.In Nicholas Long's return for 1792 of the Caroline County Land Book Alterations (of which I have a copy courtesy of Hazel Roche) one finds a Reubin Sanders, listed (in the "S"'s just before Richard, Thomas and Hannah Sale).It's more or less the same picture in 1791 and 1793.
The Caroline County Order Book entries of the 1770's are somewhat baffling, as they feature many appearances of a William Sale who was actually married to an "Ann."However, it's not clear (to me, at least) whether this was the same individual who also appears in numerous records of Halifax County, NC during the same general timeframe.Evidently toward the end of 1770, this William Sale, along with Thomas Sale, John Sale and Mary (Sale) Stewart (& her husband Henry Stewart) sued the children of the late Robert Sale (viz., Samuel, Eliza[beth], Robert, Patty (=Martha), Mary , John and William Sale) in chancery.Whether the 1773 deed from Esther Sale to these children resulted from the litigation is not clear to me, but I would surmise that the two events were both related to efforts to settle Robert Sale's estate.
With more time to study my notes and pull things together, I could say more on this subject, but will let this suffice for the time being.