I have wondered if the Leonard Sides b 1786 who married, first, Suffy Miller and second, Sarah Fogleman and went to Washington Co, IN could be a son of your Leonard Sides. Leonard didn't marry Katherine until 1803, which would make him roughly 37 years old. That would have been enough time for him to have had a first wife and at least one child, Leonard, Jr. The Indiana Leonard named one of his children Christian, who I believe to be the father of Leonard b 1766. Christian, (the elder) died April 20, 1803 (his last will and testament proven by Jacob Miller, with letters testamentary to Lenard Sides. This Leonard was a baptist.