In what ways does Willy not fit into the definition of an average working man building a secure home for his family?
Miller develops Willy Loman with such complexity that he does not fit into the stereotype of the typical working man. Sure, he works very hard for his family, he tries to raise his sons the best way he knows how, and he attempt to provide his sons with a secure future. But this play is far from "Father Knows Best" or "Leave it to Beaver." You're probably too young to know these sit-coms, so never mind. The movie American Beauty is probably more applicable--things are not so wonderful for that family either.
Willy has many shortcomings as a husband, a father, and a provider--the traditional roles of a man. He cheats on his wife and treats her with contempt. At times, her most innocent comments make him lash out at her. He favors Biff and ignores Happy. He teaches Biff that stealing and cheating are okay as long as you're "liked." He values popularity over studying; image over hard work; dreams over reality. He is haunted by the flute music of his father who abandoned his family, and admires his older brother Ben who did the same. His image of a salesman is Singleton, whose funeral is attended by his business associates, not by family and friends. And he is haunted by his own past--his infidelity and missed opportunities with Ben.
He vacillates from adoring his son Biff to having utter contempt for him. He wants more than anything for Biff to become a financial success, and refuses to acknowledge Biff, the drifter. He can build a sturdy front stoop for his family, but he disdains this type of work and instead remains doggedly determined to make a living as a salesman, which has never been that lucrative for him. In all his career, he has not earned the respect of his coworkers; he believes they laugh at him when they see him.
The image of Willy trying to plant seeds in the dark is indicative of his success as a man. Nothing of significance to him has flourished. His death is one last attempt to provide for Biff. He kills himself so that Biff can get the insurance money for another chance--a stake that Biff does not even want.
So, no, Willy does not fit the stereotype of a hardworking man who loves and provides for his family. He is instead a complicated and paradoxical character who is intriguing to study.
In the play "The Death of a Salesman" one of the things that is different than Willy in his search of the American dream is his cheating on his wife. He wants to provide for his family but he also gives the things he has bought for his wife to the girl.
Willy becomes mentally unstable in the end of the play and kills himself. Many people search for the American Dream but do not attain it. Instead, they move on with less. Willy kills himself.
The other big difference has to do in the way that the family lives in a world of lies and rose colored glasses. No one really faces the short comings of one another.