Here is a picture of Gladys that Jack Jennings sent me:
There is some conflicting information about Henry's wife's date of birth. It should be Nov. 8, 1889. Here is what Ronny wrote on this indicating that the 1900 date does not pan out very well.
Regarding the dob of his wife Gladys. The SSN DBI gives the date as 8 Nov 1900. She was 28 in Jan 1920 and 30 in April 1930. In 1930, Gladys says she was 1st married at age 21, that means 1921. Henry said he was 1st married at age 24, that is in 1910... If born in 1900, she would hardly have borne Sydney at age 12.
And here is some more info from Jack Jennings:
About Aunt Glady's DOB - According to the notation in our family Bible, Aunt Gladys was born November 8, 1889. She was the oldest of my father's sisters. This is also the date found in "The Jennings of Haddonfield" by James R. Jennings , May 1967, Pheonix, Arizona.