I felt as though Socrates never truly followed his point of “believing the other”, and that he often did semantics or in some way purposefully misunderstood what his opponent were arguing. It felt very disingenuous, especially because it was written by his pupil and had - to me - a very large “then everybody in the bus clapped” vibe.

Some of this is probably coming from the fact that Plato's rendition of Socrates was basically just a pedagogical device designed to communicate Platonic philosophy to upper-class Greek dudes. Socrates' interlocutors spend half of most of the Platonic dialogues just saying shit like "yes Socrates," and "indisputably Socrates," and "you're so wise Socrates" because the dialogues are basically just argumentative essays meant to give Plato's views. The people Socrates is talking to (at least in most dialogues; there are some limited exceptions) are just there as rhetorical devices, much like questions in a standard (i.e. non-dialogue) essay today.