I think that Willy and Troy are very similar to one another. One point of similarity between them is the pressure they feel from the outside world. Willy's fundamental force of being in the world is the desire to "be somebody." His need to translate his efforts and what he does into material success in order to appropriate what he considers to be "the American Dream" is something that is an indelible part of his personality and characterization. Troy experiences the same types of pressure in terms of his desire to make money and reflect money as a form of success. One significant difference here is that Troy is more concerned with critiquing the social configuration that surrounds him. He raises the issues of class and race in how Black men try to endure and succeed in such a setting. Willy does not make any sort of external critiques. If anything, he is more convinced that the system of what defines "the American Dream" is correct and all those who speak out against it are wrong.
Another similarity between both men is how they interact with their families. Willy is blinded by his own desire to be successful, to a point where he cannot see the emotional damage he is doing to his own family. He believes himself to be a "more loving father and husband" in his flashbacks and his own conception of self. However, this is not something that he can bring himself to admit outside of these moments. He is not able to bridge the gulf between his own vision of self and the reality that he presents. Troy is similar in that he takes on the role of provider to his family. However, where Troy is different is that he harbors no such illusion of his own emotional quotient. He is quite open about the fact that he does not fully interact on an emotional level with anyone to a substantive level. He is caged by his own "emotional fences," and while he might lack the affect to be able to articulate it, he understands this reality. This is something that Willy does not do.
A significant difference between both characters is their view of death. Willy embraces it as a way to "make something" of himself in terms of his life insurance policy with the money left to his family. For sake of "being something," Willy is able to embrace death. Troy is not able to do this. Troy's fear of death, his desire to keep it away, to do battle with it, to build a fence to wall himself off from it, is where he is very much different from Willy. The finality of death and the fact that in its face, so much has to be reconciled is something that Troy cannot face. It is here where he and Willy feature significant divergence from one another.