Jim, I don't think there is any connection with Lewis G. Pyles/Piles and Reuben and others you have mentioned. My L. G. Pyles (sibling of my gr gr grandmother, Frances Sophia Pyles) was born c1834 to Charlotte Wynn/Winn of Savannah, GA & Col. S. R. Pyles of Glynn Co., GA. His father died c1836 and mother was killed in 1842 on the Florida frontier. His older brother, S. R. Pyles (Jr.) was guardian to Lewis until he reached majority in the 1850's. He first sent him to Rye, NH for his education in the 1840's, but Lewis returned to Florida with a good case of home sickness. He later went to Thomasville, Thomas Co., GA where I suspect he received his final education. There, he met and married Edward Remington's daughter, Mary S. Remington. they moved back to Newnansville, Alachua Co., FL where she died giving child birth. Their surviving son, Samuel R. Pyles (1856-1919)was also orphaned on the death of his father, L. G. Pyles in 1866. His maternal grandfather, Edward Remington took him to Thomasville where he was raised. Unless there is some connection to the Thomas Co. Wynn or Winn families of Charlotte Wynn, I have never been able to figure out why Lewis G. Pyles ever went to Thomasville in the 1850's. Otherwise, the Piles/Pyles family were in southeast GA as early as 1754-56 near Sapelo Island and for sure what became Glynn Co. when it was formed. Hope this helps you discern between the Pyles. I lived in Tallahassee twenty years ago and am familiar with the GA southern border Pyles too.
Charles