Legalistic, or grace?

Talk about whether something is "legalistic" always annoys me because it is such an unhelpful word.

"Legalism" is not a clear category at all, and everyone who uses it seems to mean something different, so it's no longer a meaningful word. It's an emotionally loaded term though, so it does have a meaning of a certain kind - it effectively acts as indicating a negative value judgment. ie "it's legalistic" says more about the fact that the speaker places a negative value judgment on the referent than it does about actually describing the referent.

The opposite of "legalism" seems to be "grace", which is a word that is just as bad. I have heard people use the world "grace" to mean at least a dozen different things. It also indicates a positive value judgment.

Thus when I encounter a sentence like "Is it true that Judaism was a religion of grace, not legalistic works righteousness?" my eyes roll.