The issue isn't that I don't know when something that I'll say will make people angry, it's that I don't know how I can communicate it in a way that won't.

Have you used the Try Harder? Specifically, I see responses where people say "this sentence is arrogant" and you will respond with "ah, I meant to say X," which is better worded and does not come across as arrogant.

Now, sometimes they have specific information--"the comparison to Y is what makes it arrogant"--and the improvement uses that information. But if you asked yourself "What is the minimal claim I want to make here?" you might be able to drop the dross just by dropping everything unnecessary.