This is tremendous reading! Almost every one of these stories would make a book in itself and I would want to read every one of them.
My maternal grandmother was left at an orphanage as an infant, grew up there and married my Swedish immigrant grandfather. They had just two children, a daughter who died a day or two after her birth and my father. Dad was six when his father was sent to Leavenworth Federal Prison for cocaine dealing. Dad said the local papers called him a "drugkingpin." This would have been about 1918. His father died in prison of tuberculosis. My grandmother was left to earn a living for herself and her son and among other things, made bootleg liquor during prohibition. She was caught and went to jail for a year, leaving her young son to fend for himself. He dropped out of school, 7th grade, and went to work driving a cab.
Later she was a union organizer in Toledo, Ohio, and worked in factories until shortly before she died when she was in her 50's. I loved her. She always had decks of cards for us kids to play with, gave us her pocket change, and let us spend the night with her frequently. (She stopped at her house once on her way home from work. Several co-workers were with her in the car and she bragged as she was leaving, that her grandchildren never asked her for money. And as she said that, my brother and I were running to the car yelling that she had forgotten to give us our money.
Dad never told us anything about their law-breaking until a few years before he died, then in his 0s.
Maternal grandmother was born in Quebec, the oldest of several children. Both of her parents were killed when she was 18, and the younger children went to live with other relatives while she went to Alberta to work for a family who had moved there from Quebec. My grandfather and his brother had a dairy farm in Alberta and met my grandmother when he was delivering milk to her.
She raised seven children, and was the perfect grandmother who baked cookies, and the best doughnuts in the world.
My maternal grandfather's mother was another, and fascinating woman, but I've taken more than enough space so I'll quit.