1. Yes, that's true. However i'm not sure I see clearly the distinction you're trying to draw here. You could build a neural network that can ask clarifying questions too. You can certainly define an ML model that recognizes one right answer as well: just pick the answer that has highest probability in your softmax output.
2. Well, there are a lot of ways to do this in principle, but word vectors in their original form are themselves latent attributes. All modern NLP is based on this concept already. Let's look at the 'suitcase' example in the article:
> The trophy did not fit in the suitcase because it was too
> 1a. small
> 1b. big
In NLP this problem is generally called "coreference resolution". That is, resolving which prior object a given pronoun is referring to. The ambiguity of this problem is indeed very subtle, and probably quite hard for an ML algorithm to learn. You can look at a parse example here:
https://huggingface.co/coref/
This is a near state of the art coreference resolution model, and it indeed fails to properly resolve here. Although you do see that the probabilities do actually shift towards the right answer, which is (very weakly) suggestive that it might be beginning to learn it.
So, trying to unpack what's going on here linguistically, the essence of the problem is that the relation between "it" and "trophy" vs "suitcase" is contextually contingent. The necessary context is that trophies go inside of suitcases, and not vice versa. You then need to understand how the concept of insertion relates to sizes. Putting thing A inside of thing B requires that thing B be larger than thing A. This is certainly a subtle, context-rich problem.
In order to try to solve this problem, a model would need to have a more structural understanding of language. You indeed cannot learn this problem based on simple word frequency counting, for exactly the reasons they state. However, even though the frequencies of big/small may be equal, there are more nuanced conditional probabilities that are not. Conditional on the latent concept of insertion, the pattern relating object size to coreference should be very statistically apparent.