Here is an obit that someone sent me several years ago that may help tie this family together.I believe the brother listed as Jimmy DeBoard may be your grandfather and also the James DeBoard (1880-1909) buried in the Beulah Cemetery. The father listed in the obit as Houston DeBaord is almost certainly David Houston DeBoard (1855-1933) that is also buried in the Beulah Cemetery.
However, there are some problems with the above.David H. DeBoard married Mary E. Toppins on 17 July 1881 in Iron Co MO.However, it appears this James DeBoard was probablyborn in late 1880. It appears that Houston and Mary Toppins were either divorced are Mary Toppins died in the early 1890's and their children were raised by relatives and/or others. Houston remarried to Mary Hinkle sometime around 1900. Mary was previously married to Alexander Bennett abt 1894. So, Houston had children by his first marriage to Mary Toppings; Mary Hinkle had children by her first marriage to Alexander Bennett.Then Houston and Mary Hinkle had children of their own.
Bertha Aslee DeBoard is shown as Bertha Debord b Dec 1887 in the 1900 Census for Cedar Creek in Wayne Co MO and listed as a servant with Henry S. Goad (1840-1916, who was also connected with the Hinkle family, but exactly how, I don't know. Almeda Deboard b Feb 1892 is listed as a granddaughter in the household of George W. Toppins in the 1900 census for Iron Co MO. I have not been able to find James or Jimmy DeBoard in the 1900 census.
Now for my speculation re the siblings and half siblings listed in the obit for Doshia Almeia (Deboard) Middleton.
The two surviving half sisters are listed as Mrs Clum Sullivan and Mrs. Laverta Casteel. Mrs Clum Middleton is probably Lola Mae DeBoard (1905 -2002) that married Christopher Columbus Sullivan. Lola Mae was probably daughter of Houston David DeBoard and his 2nd marriage to Mary B. C. "Sissie" Hinkle sometime around 1900. Laverta Casteel (1898-1974) was probably Laverta Bennett d/o Mary B. C. Hinkle and her first marriage to Alexander Bennett sometime in the mid 1890's.
The predeceased siblings are listed as Jimmy DeBoard, Mrs Frank Hinkle and Sissie DeBoard. Mrs Frank Hinkle is Bertha Aslee DeBoard (1886-1948).Jimmy is probably your gf and son of Houston DeBoard, but not sure of his mother. I'm not sure about the Sissie DeBoard either, but I doubt that she was a full sister.
Mrs Almedia Middleton Mrs. Doshia Almeia Middleton of Flat River died Feb. 1, 1966, at the Bonne Terre Hospital at the age of 75.A daughter of the late Houston and Mary (Toppins) DeBaord, she was born Jan. 17, 1891, at Sebula, Mo. The body was in state at the Caldwell Funeral Home in Flat River where chapel services were conducted Friday Feb. 4,at 2 p.m. by the Rev. John Doolittle, assisted by the Rev. V. E. Defreece. Interment was io Parkview Cemetery. Mrs Middleton was married to Lee Davis, now deceased.Two children born to this union survive; they are Mrs Dallas (Mary Irene) Probst of Elvins and Leeman Davis of Potosi.She was later married to Charles Middleton. Three of the four children born to this union, twins Jessie and Lessie and Mrs Gearl (Murriel) Seabourn, preceeded their mother in death. Surviving is a son, Charles Middleton, address unknown.Other surviors include:two half-sisters, Mrs Clum Sullivan of Des Arc and Mrs Laverta Casteel of Piedmont; 31 grandchildren, 26 great-grandchildren, several nieces and nephews. Mrs Middleton was preceded in death by a brother and two sisters, Jimmy DeBoard, Mrs Frank Hinkle, and Sissie DeBoard.