You never know in baseball when a moment will turn into that.
I agree that you need to take the situation into account, but the “borderlineness” of a call should be taken into account, too. If it’s an egregiously bad call that you know you’re going to win, I am fine with challenging it regardless of situation. I think we know those when we see them.
If it’s borderline, absolutely, consider the situation and score.
From what I can tell so far, batters are too eager to challenge and pitchers/catchers are too reluctant. Seems like batters are forgetting that a pitch that just barely clips the zone is the same degree of a strike as a pitch right down the middle.