Some cool shadow related words: Albedo, Penumbra, prefix-Umbra (Antumbra), Terminator and Occlusion. One could spend hours talking about surface reflective indexes, unreflective bodies and shadow stuff so I'll just stick to basic OP.
In one sense shadows are holes (in the cast light) so the question becomes 'can holes have holes?'.
A shadow cuts a generally conical hole in the uniform field of light. The cone tapers off to a point if the blocked light source is larger than the covering body or it broadens its base at an angle originating from the smaller light source.
We also say that a light is cast from a source, but a shadow is cast from the occluding body which blocks the light.
How to make holes in holes?
1. By making a hole in the occluding body we get a light cone that cuts a hole in the larger shadow cone. Same if light is shone in a way that doesn't intersect the occluding body but still falls on the umbra.
2. By shining light on the surface covered in shade we make a hole extending towards the occluding body.
3. If the surface under the shadow is uneven, there can be areas covered by shadow and other areas placed lower where light from somewhere else disperses the shadow.
How to cheat holes in a shadow?
1. Close your eyes and imagine light.
2. Imagine that shadow is a cone of light and the area that is in direct light is a shadow.
In another sense 'shadow' refers to the emergent phenomenon of light being blocked So, if an area within the bounds of a shadow was unblocked form the light source it could maybe be considered a 'hole in the shadow'.
What if a light source casting the shadow shines only 60 times per second and goes dark 60 times per second like a lightbulb? Can we make two lightbulbs with one going off 70 times a second and another 60 times a second and get 4 types of holes in shadow? A shadow when both lights are on, shadow with only light A, only light B and no light.
In yet another sense a hole has depth and shadows have no depth so they can't have holes.
Isn't a shadow itself a hole in a light cone? If a shadow on a 2d surface has spots where light shines then these will appear as 2d holes in a larger 2d shadow hole in a light hole and so on.
A few takeaways from thinking about holes in shadow:
Conjecture: Holes, shadows and light sourcess are concepts only understandable by entities able to visualize or perceive in 3 dimensions
Conjecture2: If visual perception and the subject of a sentence are taken to mean the focus of human attention then: A hole is either the focus of perception, or a place entirely omitted by perception OR A hole is the subject of the sentence or a background feature of a long list of items.
Conjecture3: Language relies heavily on the human visual cortex and our ability to see things or remember shapes that we've seen. Can a blind bat describe a shadow, probably yes, but it will be a sonic phenomenon.
What do holes tell us about language: That language is organized in a very similar way to how our brain organizes the sensory input that we perceive. Both language and perception has the focus of attention which is the subject of the sentence or sensory input. They both have a moving context, just as focus of the attention shifts from one sensory input to another so does the new sentence move from one idea or abstraction to another.
Surprise final conjecture: If our primitive brains developed in blind organisms and evolved into organisms with visual perception, then the focus of attention existed before visual input. This means that our brains primary mode of organization is having a mental focus and background on things this is either because our senses evolved this way, or it has to do with how our thinking works which then influenced both our perception and language.
This probably means that thinking precedes language and sensory input. Our senses and speech just organized itself around primitive thought structures that we didn't have words for.