Robert and Josephine continued to live in the Cowan family home in Eufaula. Josephine would also help out with the other Cowan siblings and assist her with other duties of the home. Sometime in the spring of 1862 Josephine would learn she was pregnant and this would have been a jubilant time in the home, but for the fact that the Civil War that was raging all around Eufaula. The town was fortified with many soldiers from the Confederate Army. There was a Confederate hospital located inside the borders of this occupied town. Eufaula was built along the Chattahoochee River so it would have been an excellent place to transport injured soldiers and bring in much-needed supplies. There is no evidence that Dr. Fleming would have assisted with the wounded soldiers or not. The Confederacy had its own doctors, so it's unlikely he would have been involved with that.
Later that summer Dr. Fleming, while sleepwalking, fell from the second-floor balcony to the porch below. The accident left him paralyzed and confined to a wheelchair for the rest of his life. He and Josephine would later move to Union Springs. Dr. Fleming took a position in county government as a Register in Chancery and was a well-respected businessman.
Around 1868, Josephine's Mother, and youngest sister, Willie, who was about 11 years old, would come to live with Robert and Josephine. This would be wonderful news to Robert and Josephine's only child, Lola who was 5 years younger than her Aunt Willie. These two would become more like sisters than aunt and niece.
Josephine would care for her ailing Mother, Anna until she passed away in 1869. Now, the 12-year-old Willie was orphaned. Naturally, Robert and Josephine would continue raising her as their own. Willie and Lola were very close and almost inseparable.
From my research, I believe that Josephine played piano and that she taught both Willie and Lola to play. It is also believed that both girls were educated beyond high school. Willie may have been a very gifted pianist as well as accomplished vocalist. She was also quite beautiful and as I have read in my research, there are many descriptions of her loveliness. Willie continued to live with Robert and Josephine Fleming until she was 26 years old. She had caught the eye of a young man from Union Springs by the name of Robert C. Jelks.