Could it be that the Ian-Holly path ends if you cancel the first meeting on the 2nd day, if you go to lunch with Alison instead? I feel both of them hardly talk to each other afterwards.
Once again this is kind of tricky because if you want to do both Routes (Alison and Holly) it is important to choose Holly in Chapter 1 when you have to decide if you meet with Holly or Alison for lunch but then in Chapter 3 when you have do decide again if you meet with Alison or Holly/Lena you should choose Alison (if you want to continue the relationship with her and also want to see every Scene with her) but you still can progress Holly after this.Yea Holly's path is closed off if you choose to meet with Alison for lunch.
Long story short you won't be able to do the book switcheroo with Minerva as a result of seeing Alison for lunch, and you won't be able to go on the date with Holly. I think it has to do with the agenda points. A while ago someone here even posted the requisite number of points to trigger the events.
I remember last time someone said you don't have to meet Alison in Chapter 3 to progres her Route?! But you will still miss one of her good Scenes if you don't meet with her in Chapter 3.