I would set Waiting for Godot in a playground, around the park bench area where parents and seniors usually sit. This park would be in a deteriorating condition, but still recognizable, with the tree shading the park bench. Estragon and Vladimir would be around late middle age or early senior age. The park bench, rather than the park, would be the center of their world. The combination of their age and the state of the surroundings would emphasize the themes of waiting and add a hint of neglect to the story.
I would make the boy very present in the background, which is the playground. In very dim and shaded lighting, the boy would sometimes swing around on monkey bars or go down a slide. He would never be noticeable enough to attract the attention of Vladimir and Estragon. Maybe he would laugh in the background sometimes too. This carefree, deliberate, and almost gleeful action would constantly contrast with the unchanging nature of the main action of the play.
Pozzo and Lucky I would cast as a young, cocky “finance bro” and a clumsy intern. I think this would add an interesting layer to the relationship between Lucky and Pozzo, especially in today’s society. Their appearance in the second act would show how they, or rather Pozzo is not a powerful actor in their world either. Estragon and Vladimir, as they age, would keep on waiting, while the boy keeps playing in the background.