Niya, I think you are taking the wrong lesson from what you are doing. If you take your alleged pseudo-example (it seems quite plausible to me, so I wonder just how phony it really is), you aren't really doing what you said you were doing (I'm too lazy to go back and find your actual quote). What you are really doing is pointing out a contradiction in a set of beliefs. This is not appreciated in ANY setting, but it is highly valuable in nearly EVERY setting.

We never really understand the world around us, nor do we ever really understand any programming problem. All we ever do is build up mental models to represent the world, then act on those mental models. To some extent, every one of those models fails to accurately represent reality, but it is relatively common for a group of people to accept a common mental model (though each individual has an actual understanding of that model that differs from all other members of the group). As a general rule, we need those models to be able to function in the world, but we often fall into the mistake of believing that our mental models ARE reality rather than just an imperfect representation of reality. All you were doing with that trolling example was exposing a flaw in the model held in common by some set of people. I think Socrates used the exact same technique, and did so in the same way (at least, that's my mental model of what he was doing). Had you opened with stating that you wanted to show that they had a flawed model, they would assume that you were an enemy to their views and would pre-reject whatever you had to say. From that perspective, they would reject even reasonable things you said (you see this in politics nearly every day). Instead, you open by posing as a co-believer in the model so that they accept you, then extend the model in a logical fashion to the point where you expose a contradiction in the model (even a casual student of the bible would see that Jesus both loved and hated people with fairly equal fervor, and he certainly wasn't always accepting or forgiving). Socrates made use of this technique to tear apart people's understanding of the world around them. As programmers, we are generally pretty used to doing the same thing to ourselves when working on difficult problems.

Whether it is good or bad to highlight the flaws in the mental models we use to view the world is entirely situational. I don't think it is inherently right or inherently wrong. At times it is necessary, since it is the source of inspiration and understanding, but since the mental models allow us to function in this world, there are times they have to be left alone.