There have already been several attempts to procedurally generate Where’s Waldo? style images since the early Stable Diffusion days, including experiments that used a YOLO filter on each face and then processed them with ADetailer.

It's a difficult test for genai to pass. As I mentioned in a different thread, it requires a holistic understanding (in that there can only be one Waldo Highlander style), while also holding up to scrutiny when you examine any individual, ordinary figure.