What are the obstacles or hurdles in Holden's way?

Holden presents his story to the reader in a conversational and almost naive manner, revealing elements of his personality and personal details of his life without a fully developed sense of self-consciousness. In this way, he tells the reader about all of the challenges in his life. Here are a few examples of these hurdles.
First of all, Holden has a hard time with his family life. Both of his parents as well as his brother D.B. and his sister, Phoebe, are all grieving the death of Allie, Holden's brother. This tragedy, plus the fact that Holden doesn't feel he knows or understands his parents well, have led Holden to feel a bit stuck and directionless, and so he looks for answers from other people who seem to disappoint him.
Another obstacle Holden experiences is his own way of holding other people to a high expectation and then feeling disappointed when they let him down. For example, while in New York, he has an exchange with a taxi driver he has only just met, and this driver gets impatient with Holden's questions. Holden seems annoyed by this situation, but if he hadn't been so persistent in his line of questioning and so sure of a helpful response, he may not have invested such emotional energy into the conversation.
Also, Holden may have experienced abuse at the hands of Mr. Antolini. This episode of molestation is debated amongst Salinger scholars, but if it is true that Holden was a victim of sexual abuse, it may explain some of Holden's difficulties in life. Without the right care and psychological and emotional treatment, Holden may never be able to move past this obstacle.