While I can't easily read upside down text, I can instantly recognize it as not only text, but that it needs to flipped upside down in order to be read. That's something current "deep learning" AIs can't do reliably, if at all.
If I had to describe the root cause of this problem it would be that humans process "problems" rather than "things" and we "learn" by building an ever growing mental library of problem solving algorithms. As we continue to "learn", we refine our problem solving algorithms to be more general than specific. Compare that to a deep learning AI that learns by building an ever greater data library of things while refining algorithms to suit ever more specific use cases.
I think you're describing a level of generalization above the application at hand. We could easily train a neural network to recognize the orientation of a font, and then build an orientation invariant "reading" app by first recognizing the rotation of the text, transforming it so it is right side up, and then recognizing as normal.
I tend to imagine our brains works similarly. It's not that you have a single "network" in your brain that recognizes test from all angle, but your brain is a "general purpose" machine with many networks that work together. I think current deep learning techniques are great for discrete tasks, and the improvement needed is to have many networks that work together properly with some form of intuition as to what should be done with the information at hand.
If I had to describe the root cause of this problem it would be that humans process "problems" rather than "things" and we "learn" by building an ever growing mental library of problem solving algorithms. As we continue to "learn", we refine our problem solving algorithms to be more general than specific. Compare that to a deep learning AI that learns by building an ever greater data library of things while refining algorithms to suit ever more specific use cases.