Short replies are harder than long documents, and the tooling is backwards

I've spent the last year building writing tools, and the thing that surprised me most is where the difficulty actually sits.

Long-form is easy for a model. You give it a topic and it fills a page. Nobody's day is blocked waiting on a page.

The two-line reply is the hard one. To get it right you need to know what you're replying to, what was said three messages ago, what you already promised this person, and how blunt you're allowed to be with them. That context is scattered across a thread, a file, an old email, and your memory. So the ninety-second reply takes six minutes, and you do that forty times a day.

Almost all the tooling went to the long stuff, which was already the easy half.

I'm curious whether this matches other people's experience, or whether I've generalized from my own.

Where does the time actually go for you, and what have you found that helps?