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To speed things up I did not pick up any tapes or the father's letters in my third and fourth playthrough. The tape below the lodge does not seem to be a requirement for "Move On".
Also I don't think it makes a difference whether you walk to Dark Rouge or take the boat. The final goodbye scene is always by the tree on Little Rogue, so Riley will somehow make it back there in any case.
- I did find and read the tape in the tree trunk.
- I did explore the boathouse, which means that I had to go to the last island on foot. I still got the "Move on" ending, so having the boat is not required.
- During the drowning scene, I do not remember exactly what I picked, but since I was generally dismissive of Josh throughout the game I chose response that were geared towards my player character staying alive and being very direct in telling Josh that he is killing her.