It sounds to me like you have a lot more info than I have! I've only just begin by entering what my father's research said in the early 80's, and he didn't have too much back on the Coles, though he had more on the Ryersons. My next step is working backwards from myself to "confirm" my father's info and build off of that.
Olive's brother Elmer had a daughter, Millicent Cole (still alive), and her son Kenneth is my father.
I'll send you access to my tree - I'd be happy to compare notes.