How does Willy's inability to deal with technology connect to his lack of success as a salesman?
I think that Willy's lack of familiarity with technology represents one more domain of how the world has changed without him in it. Of the many challenges Willy endures, one of them is the idea that the world's configuration of what a salesman is or what success is has massively changed without notification to Willy. When Miller argues that the play is about "the matrix" that confronts modern consciousness, this is a part of that design. Invariably, there are advances in technology that, while making life better for many, does rule out some and "delete" them from the programming design. This is certainly where Willy is. The idea of being a salesman has changed for Willy. It no longer is defined by what it used to be. In this light, then, Willy's struggle with technology is akin to the larger fight where he and the modern individual are "struggling with forces that are far greater than we can handle, with no equipment to make anything mean anything." In the end, his failure with technology is strongly connected to his lack of success as a salesman and in achieving his dream.