I think you are on the right track.
The problem is, "specifity" has to be handled in a really specific way and the intention has to be the desire to get from the realm of unclear arguments to clear insight.
If you see discussions as a chess game, you're already sending your brain in the wrong direction, to the goal of "winning" the conversation, which is something fundamentally different than the goal of clarity.
Just as specificity remains abstract here and is therefore misunderstood, one would have to ask: What exactly is specificity supposed to be?
Linguistics would help here. For the problem that is negotiated grows out of the deficiencies of language, namely that language is contaminated with ambiguities. Linguistically specific is when numbers and entities (names) come in.
With "Acme" there is already an entity - otherwise everything, even the so-called specific argument - remains highly abstract. Therefore, the specificity trick in the dialogs remain just that - a manipulative trick. And tricks don't lead to clarity.
Specificity would be possible here only by injecting numbers: "How many dollars does Acme extract in surplus value per hour worked by their workers?"
After that, the exploitation would have been specifically quantified and one could talk about whether Acme is brutally or somewhat unjustified exploiting the workers' bad situation or whether the wages are fair.
The specific economics of Acme would, of course, be even more complicated, insofar as one would have to ask whether much of the added value is already being absorbed by overpaid senior executives.
At the end of any specific discussion, however, the panelists must ask themselves what they want to be: fair or unfair? Those who want to gain clarity about this have to answer it for themselves.
Then briefly on Uber: Uber is a bad business idea. It's bad because it can only become profitable if Uber dominates its markets up to the point that they don't have no competition anymore. Their costs are too high. A simple service is burdened with huge overhead costs (would have to re rechearched specifically, I know), and these overhead costs are then partly imposed on the service users when user are in desperate need, partly on the service providers.
Even with Uber, you can debate back and forth the specific figures for a long time. In the end, users have to ask themselves: Do I want to use a business model that is so bad that it can only exist as a quasi-monopolist?
I don't do that because I don't want to.
If someone like Peter Thiel, for example, is such a bad businessman that he only can survive in non-competitive situations, then he might say: Zero competition is my way of succeeding since I can't make money as soon as there is some competition. Fairness doesn't matter to me.
Hoewever, Specificity is healing. That's right. When one talks, one can never talk specifically enough. However, many ideological debates suffer not from too many abstract concepts, but often from false specificities. Specificities, after all, are always popular for setting false frames. In the end, clarity is only achieved by those who really want clarity, and not simply by those who want to win.
Thank you for this great and well thought article on a topic of "kindness" that interests me in connection with the big puzzle: "how do people understand what people are meaning with their words?" In my observation, the process of understanding is not yet fully understood, except where understanding takes place without language.
In all the situations of ambiguity you describe, we again encounter the problem of language, that even clear and unambiguous sentences can be understood differently. And this is even possible in situations in which the context is shared by the speaker and the listener. In fact, even apparent sentences can be particularly difficult to understand if it remains unclear why they are being said.
Interestingly, this is always immediately the case when people have unfriendly feelings towards each other — the evidence for this is provided daily in heaps on social media (where the vast majority of "debates" revolve around the meaning of words and sentences that the other side supposedly misunderstands).
This leads to a surprising hypothesis: people can only understand each other in conversations when their minds are friendly towards the person they are talking to. Kindness means: I understand or want to understand what is happening inside you.
Suppose you understand this and really want to be friendly. In that case, every embarrassing situation is “easy” (in fact: nothing comes easy in human communication) to resolve:
1) Start a dialog: If there is the slightest embarrassment or uncertainty about a motive, always ask: "Do I understand you correctly that ... ?"
2) "Please" is reciprocal friendliness in advance and an underestimated factor for successful sociality.
3) Communicate your own feelings when there is an embarrassing moment. Allow your conversation partner to recognize how you feel.
4) Smile. It is no coincidence that we live in the era of "smileys", the substitute signs for facial expressions and gestures. Smiling is a key signal for the willingness to understand the person you are talking to because you have no bad or rejecting feelings towards her. Unfortunately, men tend to lack expression. In the clips (Tik-Tok, YouTube, etc.), however, we see how smiley faces are increasingly being imitated in real facial expressions. This seems cartoonish and silly, but can be explained by the concern that the words spoken alone could be misunderstood without further signals for "intention detecting".
In my eyes, however, humans much to easily fall into the loop of misunderstanding. There is no such thing as non-ambiguity. And when hidden feelings are involved, embarrassment is difficult to avoid. It even happens to lovers.