This is the oldest Gluckhaus board I have found so far. It is dated on the painting! Brett für das Glückshaus-Spiel, oberdeutsch, 1583 Buche, bemalt mit Wismuth und Tempera Bayerisches Nationalmuseum, München
This is a portrait of a German woodturner from the early 1600s. It is from a book with page after page of portraits of craftsmen. They are interesting because they are of very specific people; instead of just illustrating their roles they reveal the people.