With Swap 3 out of the way (and you should play both Isle of Dread and Summoner's Soul and give both games all the Misao nominations. ALL OF THEM!), I can start to focus on this again.
One of the things I wanna do is put together a calendar of events. This should help me writing up NPC dialog in their reaction to those events, as well as serving as an outline of the game's story progression.
I absolutely want to move events around so that Day 13 is when Jin texts Izumi about going to Iwayama, but doesn't force the player onto Iwayama that self-same day. The game will be stuck on Day 14 until the player decides to attack Daichi, rather than lock them in the dungeon with no hope of survival. Playtesting this "loop", and the Day 28 "loop", will certainly be in order.
As far as the in-game event calendar is concerned, chapter 3's end intends to be on Day 42, and the writing is up to around Day 41. To put it another way, the event that unlocks the boss fight for Day 42, and for Day 42 to "loop" until that boss is fought. I probably haven't made any maps for Chapter 3 yet, so, I've got that to not look forward to!