You know, like you, I resonated with this idea that I'm fundamentally philosophical, but not into philosophy.

Recently, I've taken a philosophy of science class that worked as an elective towards my degree. It was honestly great. There's plenty of poor philosophy out there but certain subtopics are good. Sounds like you may be into the philosophy of mind.

Your empirical views would probably align with David Hume to some degree (mine do).

I've thought deeply about "uploading" my consciousness into a machine. But it's like you said, the process would likely involve making inferences based on neurological structures, and providing some form of representation of this. It really seems like you externally, but likely not you.

This is probably due to the limited perspective bounded to the limitations of human cognition. We considerably simplify everything and represent it symbolically because that's how we make sense of the complexity of the universe. How can we ever get an adequate representation of ourselves if we're only capable of understanding things truly after a great reduction or simplification? Brings you to one of those, "can a mind understand itself" type questions.

Many agree that the prevailing force of the universe is an increasing entropy. They ultimately believe that we'll reach thermodynamic equilibrium through this. This is contradicting in my mind, supreme order built from increasing disorder (randomness). Diffusion is everywhere so this is likely true, but as a thought experiment could it be that we just don't have the capacity or perspective understand this complexity? Is it truly random or extremely predictable from a higher level of perspective and knowledge?

This is all a really long way of saying, hey man, we probably just aren't smart enough to ever realize a true representation of ourselves. It's like attempting to define a word that we all know, but can't pin down. Somehow there's always something uncanny or off about something that is not "real", whatever that means.