Hello Carol,
I know a little about Henry James Ollenbittle, your aunt's father, but nothing about Gertrude herself. Gertrude's father was not the same Henry ollenbittle who was Stephen's grandfather, he was Stephen's grandfather's half-brother. It is all very confusing, because successive generations and even members of the same generation used the same name; Henry James Ollenbittle, I will try to explain.
Gertude's grandfather Henry James ollenbittle(my greatgrandfather) had at least 3 separate families (at the same time). Stephen and I derive from Henry James Ollenbittle's legal marriage (to Eleanore Bennett). HJ Ollenbittle was born in 1852 to differenciate him from other members of the family of the same name I have given him the designation III (3rd). Gertrude was born to his son Henry James Ollenbittle born to his mistress Annie Gillard in 1883 (Stephen's grandfather HJ Ollenbittle was born 1875 to Eleanore Bennett). HJO 3rd had 11 children with his wife, 7 children with Annie Gillard and 1 with a Christine (all while being married to Eleanore). Henry (3rd) seems to have used the name Thomas (to evade the authorities?). His illegitamate families used the surname Ollenbittle (even in the 1891 census).
Gertude's father not only inherited his father's name, but also his character too. What I have found out about him is as follows:-
Henry James Ollenbittle (IVa) emmigrated to Canada in 1909, but went back to England (arriving in Liverpool on 13th March 1919 from New York) and then in 1923 he returned to Canada with his wife and daughter (Gertrude). He is recorded as crossing from Canada into USA (at Buffalo) on 3rd March 1919. This Henry James had a lot of similar traits to his father, he also had a mistress, and even changed his name for two years to Harry Gilmour (he took the last name of his mistress).
It seems that his wife his wife had enough of him and returned to England where your story of your Aunt begins.
I would be very interested to hear anything about your aunt. I can provide you with more of the very colourful history of the Ollenbittle family. Unfortunately there is only a single photo of any of the Ollenbittle family that we have (this is of HJO 3rd's legal family and does not include him). If you have any photos of your aunt or her mother and father I would be very interested to see them too.
Best regards
Max Rasmussen