He seems to match most of the clues. Though, I'm not aware of a daughter who won the Caldecott Medal. I do know that Weik's granddaughter, Ann Grifalconi, was the runner-up for the Caldecott in 1987 for her book The Village of Round and Square Houses. It was published just before I started kindergarten.
Rob, I'm sorry to hear about your health troubles and I hope you continue to get better.