There's a difference between a discussion where you rationally discuss why someone's point of view does not make sense, versus actively shitting on it.

Example: kosher laws are outdated, and in some senses utterly nonsensical. For example, if the law is based on "don't drown a calf in its mother's milk," why would chicken, which is not mammal and therefore could never produce milk, count as "meat?" Pointing this out is totally fine. However, using that as an excuse to trick a black hat into eating pork? NOT COOL.

My POV is: feel free to criticize; just don't cross the line into "asshole" while doing it.