All credit for this goes to VidGamiac. I'm just porting the solution over.
There are five missable entries.
In chapter 2, at the funeral, let Snow finish her eulogy without interrupting her. As Johnny Broflex noted, you need to go to the table and look at the card on the left while letting her talk.
At the end of chapter 3, you have a choice. To be most efficient, go to Crane's apartment first, and look at the statue of the Headless Horseman on the desk on the left with the lamp on it.
At the Tweedles' office you should get Flycatcher's entry.
In chapter 5, there's a tree. You'll get one entry for burning the tree, another for not burning it. You can rewind afterward to get the missing entry.
The achievement will pop at the end of the episode.
