I think Holden Caulfields difficulties started when his brother died from leukaemia because on the night of his brothers death he smashed every window in the garage with his bare fist and said that he didnt really know what he was doing. From what I have read in the book so far this doesnt appear to have affected him in what he does. He is very quick to judge people and seems to hate nearly everyone he encounters but I dont think that this is related to he death of his little brother.
One of his problems which I think may be related to the death of his little brother is that he is continuously getting expelled from schools which is how the book starts with him getting expelled from Pencey Prep. When he is leaving the school he yells out “So long, ya morons! ” which I think is a dumb thing to say because someone may have been woken up by this and gone out to get him.
Another thing, which I believe should e counted as a problem, is that he wrote a little message at the bottom of his exam to the teacher saying that he found his lectures interesting but didnt take much of it in. Something else that Holden did a lot of was lying which I believe is a problem. He lied to another students Mum on a train about many things including what her son was like, why he was on the train and even his name. In another part of the book he lied about his age to a prostitute. He also lied about a few other things in the book.