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1st check the time stamps on the saves for how long the playtime is, it should be easy to figure out where to start from there.
2nd, there is a glitch on PS4 that will sometimes, but not always change your game to nightmare difficulty upon loading. This might make some parts difficult, but most of the saves should have enough health items to get you to the end of the level.
1. Either start a new game from fresh and collect the first 3 butterflies and notes and get the phone trophy to pop all on normal or load my save with the shortest amount of playtime and check how many butterflies are collected, and find enough to get you to 3.
2. Load the second save for the hospital with the longer playtime. Finish the hospital level to get the trophy to pop. Then check the PSNProfiles.com trophy guide to see where to go to get the third Troublemaker action for the troublemaker trophy.
3. Load the save from the school, complete the level to get the level trophy to pop.
4. Load the save from the apartment on nightmare difficulty. You will have to figure out the puzzle to finish it off. I recommend looking up the YouTube Speedrun tutorial video in the PSNProfiles.com trophy guide. You will have to fight and defeat the Glower monster to get the trophy for that as well as the final butterfly from defeating him. Complete the level and you will get the 3 ending trophies for the ending, good ending and nightmare difficulty ending.