I struggle with this question when I write. On the one hand, I sometimes feel like I am "repeating myself but with rephrasing". On the other hand, I find that those instances of rephrasing adds content. I often get accused of being excessively long-winded, yet when I shorten things too much, I get wildly misunderstood.
I find that many people don't have the context. I suspect part of it is that I don't see the world the same way most people see it. Shorter remarks rely on shared context to be properly understood. Example: In my teens, I remarked to my father that I was considering "running" (something). I was a role playing gamer considering taking up gamemastering. He assumed I meant jogging for exercise. I didn't bother to try to correct. It seemed futile.