I doubt we're discussing the same James Middleton. You describe your James Allen Middleton as having been born in 1827 in Larue County, Kentucky, and mentioned that he was living with his parents in Larue County in 1850. As I said in my earlier message, the James Middleton in Lamar County, married first to Parilee Elizabeth Moore, and second to Sarah A. Stewart, was listed in four Alabama censuses between 1850 and 1880 as born about 1812 in Georgia. His tombstone at the Vernon City Cemetery gives his date of birth as April 6, 1812. So I'm pretty sure he's not your James Middleton. I have nothing in my files on a James Middleton born in KY in the late 1820's. BUT, please, continue reading.
In the "small world" department - in today's message you name your Uncle James' parents as Charles Middleton & Elizabeth McDougal of Larue County, Kentucky, and you quote Edward Benningfield as writing "James apparently grew up with ties to the Nolin Baptist Church."
The Elizabeth McDougal of Larue County, Kentucky, who married Charles Middleton, was my 6G aunt. She was a daughter of Hannah M. Doane and Alexander McDougal. Alexander McDougal was the founder and first pastor (c. 1802) of the Nolin (or Nolynn) Baptist Church. I have a good deal of information about Alexander McDougal if you have any interest, including my own transcription from the original in the National Archives of the court proceedings associated with Alexander's Rev. War pension application. Alexander and Hannah McDougal are both buried at the Nolin/Nolynn Baptist Church in Larue Co.
My grandmother, Auggie McDougal Hays, was born in Vernon in 1887, and was a 4G granddaughter of Hannah and Alexander. Auggie's father, Cornelius Stephen ("CS"/Neal) McDougal, was the founder and first editor of The Lamar Democrat. C. S. was from Itawamba County, Mississippi, but C. S. and one of his sisters married cousins of each other from Lamar County, and both couples moved there.
Even though I don't think we're talking about the same James Middleton, I wouldn't be at all surprised to learn eventually that there is a connection between the two. C. S. McDougal was a great grandson of George Ford and his lovely wife, Nancy Middleton (1796 SC-1884 Itawamba/MS). Nancy Middleton was a daughter of Thomas Middleton (1756 NC-1832 Lowndes/MS) and Nancy Ann Baskett. I'd bet there was a connection somewhere along the line. Please let me know as you learn more.