[dragonwriter]

The principle of charity is important but also can be dangerous if taken too far, particularly, it can avoid productive discussion by what amounts to a version of the strawman fallacy where instead of inventing something that the other person didn't say shaped by one's own preconceptions to argue against, you are inventing something that the other person didn't say shaped by one's own preconceptions to agree with, which is clearly an impediment, rather than a boon, to the productive interchange of ideas.

Beyond deciding how to resolve obvious ambiguities where it can readily provide a best interpretation which it is most likely was actually intended by the speaker (the Caesar example in the Wikipedia article is a good one for this), the principle of charity is best applied cautiously to form a hypothesis of what the other speaker may have intended that can be verified through a clarification request.