The first time you said "objectively" you asked if I could objectively determine the boundary between happy life and torture, and now in this post you're talking about objective/subjective permissibility.
In the first case, limits on how precisely you can tell the happy life/torture boundary are based on uncertainty about the physical details of the possible future, and vagueness in the definitions of "happy" and "torture." It's not that in asking the question "When is that time?" there is a hidden reference to some feature of an external person (such as their utility function, or their taste in food) So I'm not sure what could be subjective of the first case.
As for whether it's objectively permissible, A: I don't believe in objective morality, because it runs afoul of Occam's razor (It probably takes a lot of bits to specify what deserves to be a potential target of moral concern. A LOT of bits). and B: even if moral realism was correct, I wouldn't give a damn (Felicifia doesn't links to individual comments, so the best I can give is a link to the thread, but see my first comment).
If you can't provide an upper bound of how long each pony will enjoy life before it becomes too entropic, then you can't prove that it will become too entropic to enjoy for every pony in finite time.
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.