It looks like we have two different definitions of 'judgment' we are working with.

The ability to

take the data of our experiences and accessible knowledge and sift through the relevant parts to apply to an idea or situation and act based on the output of that data

does not constitute 'judgment' (according to my definition). Yes, machines and AI can do that (and do it better than we can). 'Judgment' is (according to my definition), when all that sifting through the data would lead you to decide to do "X" but you choose to do "Y" instead.

Embedded within my definition of judgment is the 'free will' argument. In other words, humans have free will and are able to exercise that free will by going against the data.

My short definition of 'judgment' is the ability to be 'rationally irrational'. I am 'irrational' in the sense that I am going against what the data (or algorithm) would tell me, but I am going against the data not out of some randomness or whimsical nature, but because I sincerely believe it is 'best' to go against the data. I may not even be able to explain 'why' I am going against the data, but I am actively choosing to do so, nonetheless.