Honesty and readiness to correct renders any claim as useful as a question for learning.

I agree, though it is less direct than a question. It requires that you first create something, then allow it to be destroyed, and THEN ask the question you could've asked in the first place. To be clear, I am not saying this is "bad" (or "good"), I'm just observing.

Do you have any comments on why the process as I laid it out is something other than 'observing without judgement'. What exactly is this judgment thing? Alternatively, you can explain what you mean by 'observing without judgement' and I can try and grok it.

"Judgment", in the way I used it, means "concluding the inquiry". It's not pejorative, it just means investigation complete, conclusion reached, facts known, reality established. I am not saying that this MUST be the definition of the word, but rather, I am defining it so you understand my meaning. I'm happy to use another word if that's easier to understand.

This starts to get very tricky very quickly, because I don't have access to your internal thought-stream, perceptions, intents, etc. I am definitely going on my own (flawed) interpretations based on observations I try to make as lucidly as I know how. During our conversation, it appeared to me that you were repeatedly making claims that were based on unspoken and unnecessary assumptions, which when examined, dissolved somewhat.

For example, the claims you made about definitions were based on at least one other more basic layer of a priori "fact" about "the way things are". If there is a "way things are", that is judgment about reality. Making any positive claim about reality is judgment, even if the point of the claim is to eventually be destroyed to reveal "truth" more clearly. To observe without judgment would be to steadfastly avoid arriving at the conclusion of the investigation.

Is there a point at which no more questions can be asked about a thing?

In my experience, it is only possible to make "true" claims about claims themselves; because claims/propositions are essentially tautological. Either something is true because of it's trueness, or it is false because of its falseness. Can we really say anything else with certainty?