Although I haven't yet found LeFlore Dillard in either the 1910 or 1920 censuses, I did find what appears to be LeFlore Dillard's two youngest daughters, Lawanda A. Dillard (then age 6) and Joyce C. Dillard (then age 4), in the 1930 census. They were living with their mother and stepfather at 415 Hudson Street in Ward 3 of Oklahoma City, Oklahoma County, OK. This house is less than a mile from where LeFlore Dillard was living in 1930 with his other children.
The stepfather's name appears to be Bussell B. Michaelis but is shown in the 1930 census index as Barnell Michaelis. The mother's name appears to be Iva M. but is listed in the index as Irva. She is age 25 and was first married at age 17 (presumably to LeFlore Dillard).
LeFlore's obituary, dated 14 March 1966, lists 6 surviving daughters. Among these are Mrs. Lawanda Sudberry and Mrs. Joyce Junjil, both of Oklahoma City. If the Lawanda and Joyce Dillard enumerated in the 1930 census are these same two women, which seems likely, then LeFlore was married to Iva M. (or Irva M.) in about 1922. Lawanda would have been born in about 1923 and Joyce in about 1925.
For information, LeFlore's other 4 surviving daughters mentioned in his obituary were Mrs. Marie Christian of El Dorado, Arkansas;Mrs. Irene Richmond of Seymour, Texas; Mrs. Elizabeth Brunson of Tonto Basin, Arizona; and Mrs. Zenitha Kindig of Scotsdale, Arizona. His two sons, Ted of Globe, Arizona and Joseph of Martinez, California also survived him, as did Zella, his wife at time of death.