Lending a hand trophy

Hi folks, I’m in my second play through in chapter 4 looking for platinum. Just doing Mary mission. I’ve just done the loan shark mission V picking out the money in the fisherman’s house but I don’t find the mission in the chapter 4 list. Am I doing something wrong? Don’t want to do a third time… also is possibile to earn the trophy by doing the missions in two play through? I mean 2 in the first and the other in the second or I have to do all the mission in one play though? Thanks a lot for your time