>>8062
>I have some holiday plans so I can't do a full dissection—if I dare attempt

I admit I haven't gone back to edit it further, but I'm curious if you've read further.
Is it salvagable? If I start over what worked well?

What other premises would allow/require the time loop to be reiterated? That's one of the fun things, thinking about how year two would look different based on the first four days.
And year sixty, when Anon is granted immortality, will look different based on how the ponies have adapted/been treating him.

What Jack needs, what the final run would look like, is the mane6 find and vaguely almost-coerce "just the right mare" to live with the human, who then falls in love, and forces himself to grow up so his favorite mare doesn't need to be kept on drugs or spells to stay with him.
Then when he moves on to the next host, he sees the ponies as fully equal to himself, not "talking horses that keep trying to kill him"