English_Biscuit
If I plan on going for a platinum trophy which requires difficulty modes (which is most games these days) I usually just do it on the hardest most regardless of raging as it will unlock all the other difficulty mode trophies too. Odds are if you had trouble in the easy mode then yes it will give you a much harder time in harder difficulties.
I usually go for highest difficulty first too. I checked on some of the trophies and people recommended doing them on the easy mode. I'll skip normal mode and go straight to hard.