Followed this as well, and hints too, but ran into the same problem. One thing of note: in my interface the events you describe for Day 25 are occurring on Day 26 on my playthrough.I implemented the system marks to the buttons so players cant miss the events unintentionally, so i don't ask for your save-files to check them by myself.
Guess you missed something by ignoring the hints and exclamation marks.
This is a small guide for chapter 2 untill when your problem shows up:
day 22 -> Breakfast, Use PC, Dinner, SKIP, Living Room, Sleep
day 23 -> Breakfast, Watch TV, City -> Alley, Skip, Dinner, City -> Dwayne, Living Room, Sleep
day 24 -> Breakfast, Dinner, Skip, Skip, Living Room, Sleep
day 25 -> Breakfast, City -> Alley, Dinner, Skip, Living Room, Sleep
day 26 -> Breakfast, Use PC, Dinner, Basement -> Couch
day 27 PLAY ON and don't igonre the given hints
I really need to make a scene showing MC gets eaten by a dinosaur when players ingore the hints too often!
Also, the skip button disappears on the same day that the MC is supposed to visit Dwayne. That seems to be where the script is breaking.
EDIT: using the console to force skips, following hints and exclamation marks, and visiting every location, eventually by day 30 the skip time button showed up again.
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