I have 9 children listed for Elisha and Margaret Brown Winfrey. I have their 5th child as Oliver M Winfrey b. 1859 - d. 1896 in Kansas.My records have him marrying Babe Josephine Unknown (b.1860 in Virginia) about 1878. They had one child Harry born May 1879.I believe Babe passed away in the mid 1880s and he married 2nd, Eliza Ann Barr. They had a daughter Maude in 1887 and a son Oliver Jr in 1889.They were all recorded in the Kansas state census on March 1, 1895. It is probable they had another son Joe, before Oliver Sr died in 1896 (NOT 1889). The oldest son Harry is shown as a single boarder in 1900 in Leavenworth, Ks. By 1910, as I'm sure you have found, all 3 sons are back living with their widowed mother in Jackson, Mo. I do not have any further info on Oliver's line.
I could not find Oliver living in the Barr residence... I found him in 1860 and 1870 with his parents and in 1880 with his wife Babe.