Hmm. I think it's dubious that someone would go insane and not care about anything anymore after watching their friends die. That might or might not be altering the facts of the situation, and therefore providing evidence that isn't part of the deathist position either in real life or in the story.
But witnessing death driving people insane doesn't seem like an argument in favor of death to me.
Ponies knowing about the big rip wouldn't make sense, also I don't think the author intended for it to be a part of the universe. So to the extent that this is supposed to be a fair treatment of a position in universe, it's kind of wrong to bring the big rip into it. To the extent that this is supposed to be a fair treatment of a position in real life, it also doesn't make sense to bring endless torture because of the big rip into it, because in real life there couldn't be any indestructible immortals.
It's not necessary that it be likely, only that is has happened once. The argument would be that immortality given to ponies who do not deserve it causes insanity.
I recently published Mortal, a novella-length My Little Pony fanfiction meant to introduce anti-death concepts to an unfamiliar audience. Short description:
This is a character-driven melodrama. It's not particularly rationalist, but it's very, very transhumanist. Unlike, say, Friendship is Optimal, I wouldn't necessarily recommend this one to people who don't already know the source. It assumes familiarity with the characters and the world.
I am going to talk about how I put together the story and how people reacted to it. This will contain spoilers.
This line exists so you can break out of the automatic "read everything on the page" mode if you want to avoid the spoilers.
This story was structured as something of a bait-and-switch. I watched the reaction to a previous transhumanist horsefic (yes, there's more than one), and I was struck by how easily readers matched the explicitly anti-death narrative to the "immortality is a curse" trope. Rather than fight against this trend, I decided to work with it. The first act is meant to look like a story about learning to accept the inevitability of death. Starting in chapter 3, I break further and further away from that mold until the protagonists finally rebel against the status quo.
The first chapters got a lot of people invested who I suspect would've been turned off by a less familiar opening. Once I was into the third act, I stopped being subtle and used every trick in the book to make the pro-death characters look like the unreasonable ones. Judging by the comments, there's no shortage of readers who were angry at having their expectations flouted, but quite a few seem thoughtful, and some explicitly changed their mind on the subject.