I believe a very plausible reason for Willy Loman's indecisiveness and need to appear masculine is his lack, or perhaps want of a father figure in his youth.
When he was only three years old, Willy's father apparently abandoned his family and left for Alaska. Shortly after, Willy was abandoned again, this time by his older brother Ben, who set off in search of their father, only to somehow wind up in Africa where he would make his fortune.
Willy spends his life in the quiet fear that he is not living it in the right way, or teaching his children as he should. When Ben appears to him, there is a feeling of desperation as he attempts to persuade him to stay a little longer and asks him if he's teaching his children in the right way.
Instead of looking at his life and his children as they are, he remains in a state of denial, looking to the universe for some kind of sign that he is doing the right thing, being the right man. He becomes defensive and embarrassed when someone suggests that he is not, and covers up his wounds with lies.
He ends up committing the same crimes as his own father, and abandons his children to his lies and impossible expectations, so that they, like him, have trouble knowing what it is they should be, and how to find a place in the world. And that, I think, is the real tragedy of Willy Loman. His end is an attempt to make amends; to free them from the chains of his denial and expectations, the chains of his love.
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