You were good enough to give us some of the information from various census records, but never ages for Jessie on those censuses. I took a look at the 1900. And, you never mention the name of Jessie's wife. The following give her name, including her maiden name.
TX Dth Idx thru 1976. The R.B. Biggs on the 1900 census.
Name: Rosa B. Biggs Death Date: 04 Jan 1964 Death Place: Precinct 3, Grayson, Texas Gender: Female Race: White Death Age: 88 years Estimated Birth Date: Birth Date: 27 Nov 1875 Birthplace: Texas Marital Status: Widowed Spouse's Name: Father's Name: J. M. Hays Father's Birthplace: Mother's Name: Martha Pilkington Mother's Birthplace: Occupation: Domestic Place of Residence: Precinct 3, Grayson, Texas Cemetery: Cottage Hill Cemetery Burial Place: Celina, Texas Burial Date: 05 Jan 1964 Additional Relatives: X Film Number: 2117403 Digital Film Number: 4028316 Image Number: 1602 Reference Number: cn 2557 Collection: Texas Deaths, 1890-1976
Another daughter who wasn't mentioned mentioned in your query.
Name: Bertie Mae Smith Death Date: 18 Jul 1976 Death Place: Mckinney, Collin, Texas Gender: Female Race: Death Age: 93 years Estimated Birth Date: 1883 Birth Date: Birthplace: Marital Status: Spouse's Name: Father's Name: Jessie M. Hays Father's Birthplace: Mother's Name: Martha Pilkington Mother's Birthplace: Occupation: Place of Residence: Cemetery: Burial Place: Burial Date: Additional Relatives: Film Number: 2243938 Digital Film Number: 4168242 Image Number: 1839 Reference Number: 1857 Collection: Texas Deaths, 1890-1976
On the index for TX Confederate Pensions there is a J.M. Hays who applies from Ellis Co, TX. Have you checked on that record?You never know what clue might pop up.