There are manners of speaking (and whole languages) that are more explicit and manners of speaking that are more implicit/contextual. There's a tradeoff between doing disambiguation work in expression vs. in interpretation, and people's communication preferences often determine this distribution of cognitive effort. (And for many people, one half of that exchange is
easier than the other.)
It's true that misunderstandings can arise between people who both tend to communicate very explicitly, but they're just different from the kinds of misunderstandings that occur with people who tend to leave more disambiguation work to the interpreter. I'm feeling lazy atm so idk what to say about that except that you'd know it if you saw it.
It's true that the details are messy, but in practice it's not that difficult to recover basic concepts related to such differences in personality like "more literal" vs. "less literal" in a way that's useful.
> I’m sure if I spoke to your counterparts in the scenario you described they’d say different words which also ultimately amounted to something like “it’s difficult to interpret what they’re saying.”
Yes and no. Lots of people who speak in a way that relies more heavily on (real or presumed) shared context react to precise turns of phrase from their counterparts who prefer explicitness like "Wow! You're so good and finding the right words for things.". When they do misunderstand, they're typically less likely to notice. You only usually get the "you're difficult to interpret" realization from them if you are discussing a specific misunderstanding and you come upon a logical or grammatical distinction they just can't see.
I'm not a linguist or communications scholar and idk if any work has been done to see whether related traits really form identifiable profiles or personality types or whatever, but at least some individual traits and behaviors that I associate with these personality differences are pretty easy to measure. For example: the "intuitive" speakers/listeners tend to make more use of anaphora as well as more difficult (more distance in the conversation from the referent) and more complex (the referent may not be the most recent grammatically compatible named thing/person) use of anaphora. They also tend to see more ambiguous use of quantifiers as grammatical (little sensitivity to "surface scope/logical form isomorphism").
Idk what to tell ya but there's a real spectrum here. If you fall in the middle of it, it might be easy to miss. But for people at opposite ends of it, the kinds of communication they encounter with one another are pretty unmistakable.
Relatedly, there's a single load-bearing word in GP's comment that you seem to have missed or given inadequate emphasis:
> Many people I find speak in what I would describe as tone poems.
It's that first word I've emphasized above, "many". They're not running into this kind of communication problem with everyone. That should increase the curiosity you hint at in the beginning of your comment, because it suggests that this is not the simple problem of one person assuming everyone can/should automatically understand them as well as they understand their own statements. Their experience and their self-report of it describes a structured and selective clash in communication (down to their admission/suggestion that they may be on the autism spectrum) which your reply seems to miss.