>> he views the entire halachic process of arriving at a psak as tainted by politics, and thus unreliable.
I am saying that we should strive for the opposite.
>> many of those types of shailos are very personal, and the psak very much depends on the circumstances of the one asking
exactly. I am learning a sefer now on interpersonal behaviors and after multiple footnotes with sources, it often ends with – depends on who is saying, about whom, and to whom [for example, will the person interpret information to the worse, will he get offended, etc]. The fact that mitzvot bein adam l’havero depend on the person means it calls for psak and for more learning.
I do not propose people revealing personal information here, but surely there is a lot can be learned from specific cases, carefully described. We will probably learn better if we focus that halakha, or just an advice, will be different for different people. Whether father should let his son to listen to Ben Shapiro will surely depend on the Av, on the Ben, and on the Ben Shapiro.
An old example is of Rav Salanter visiting Konigsberg merchants. He refused to speak first. Later, he spoke and suggested that he understands that ship are arriving on Shabbos, but couuld they at least not write it down? Later – could they unload but at least not load new merchandise, etc. Why did he refuse to speak the first time around? Because there was an observant Litvishe yid in shul, and Rav did not want this guy to hear these ideas.