Thanks very much for your reply Robert. You added some info I did not have. Let me reply by paragraph.
The April 4, 1748 date should be 4 Febuary 1748 as set forth in the sale of 100 acres of land to son John.
I believe the evidence is pretty strong that James was John's son.
I also cannot separate the various family members.
I somehow missed the deeding of land to James McCleary. It sounds like the land parsel was the southeast corner of the 420 acre grant. The Clark family has been a mystery but from the land location of this sale they may have bought the a part of the Nathaniel Patterson grant. This would put them on one side of James' land and Thomas Kirkpatrick on the other. Another possibility is the Clarks are related to the McCleary's and bought a part of the 420 acres.
I believe that James was born as early as 1720 but more likely around 1724. He could have been 31 or older in 1755 and old enought to be a trustee. I do believe he and his brothers were to old to serve in the Revolution and the James, John and Samuel were James' sons and that James followed them north to Kentucky.
Sorry about the error in my post. I have no idea where April 4 came from.
I agree that the will appears to John Sr,'s.
I am still digging on Hugh McClary. I believe there is a connection but have not found the link. I'll keep looking.
Robert it was really good to hear from you and to hear I'm to not to far "out in left field" Glain