I think we need to start looking at the Gray Jedi in light of Nietzsche’s concept of the Übermensch, who is a being that has transcended traditional group morality of good and evil, and has a higher individualistic morality based on their experiences to form a holistic perspective of the workings of life. An Übermensch has the ability to conceptualize and process so many angles, layers, and aspects of any given issue that they naturally formulate a more robust perspective that is aware of the many moving parts and causal factors.
Most people have an extremely limited one-dimensional perspective based on one or two layers and/or superficial causes, and they are unaware of how to expand their thinking. Their inability to improve their own thinking and expand their perspective limits their capacity to see the totality of what is actually going on in the world within them, and around them. If there was one major sin that plagued the Jedi Order in the prequels, it was that they were prone to this one-dimensional outlook and modality of thinking, and were therefore unable to perceive the deeper factors and machinations manipulating the Republic and their Order.
It’s not that a Gray Jedi is able to draw from two one-dimensional outlooks of dark and light, it’s that they are able to draw on dozens or more outlooks, and build a holistic perspective that is all encompassing. When such an ability to perceive the massive scope of life “as it actually is” is developed and refined, the traditional morality of good and evil is discarded as a simplistic and outdated model of thinking, and thus of perceiving, reality. The gray can therefore be viewed as the synthesis between two or more perspectives to formulate a higher perspective, much like in ancient alchemical practices; in short, the gray is synonymous with the philosophical concept of “Truth”.
I highly recommend looking up the concept of “multilogical thinking”, “multilogical problems”, “dialectical thinking”, and “dialogical thinking” on the glossary of terms at criticalthinking.org, which will help the reader understand the multilogical capacity of a “gray” leaning individual.