Help needed getting the "there, are you happy now?" Trophy (possible spoilers for chapter 7)

I replayed that part over five times (two of them doing full runs instead of just replaying just the first part of it or just the whole chapter), i tried all the options and I still didn't work!

Do i need to redo the whole run? Is there an easier way to find out which one is the currently worst item? I'm just missing that trophy for a platinum!!!