How are Willy's issues in the play related to the theories of Max Weber?Is Willy driven by a transcendental and irrational goal similar to that...

Yes.

In Weber's disenchatmnent vs rationalization theory the basic gist is that the changes brought by the increasing dominance of capitalism influence society, its goals, and its activity in general.

This is clearly present in Willy's character. He complains about the "changes" happening in the neighborhood. How the houses are changing, how they keep building around them making him feel "trapped" in a form of concrete jungle.

His issue is also the fact that time has not stopped for him. It has moved on, along with its changes in the economy, in demographics, and much more. And, as time moves on, Willy remains in the back, going back in time more and more often. He would wish that time would wait for him, to provide him another chance to re-do his mistakes, and perfect his life. It would not be so. Hence, his issue with being unable to catch up with the times, his stubborness in changing or adapting, and his inability to accept defeat in order to change for the better. All this is illustrated inn Weber's theory and is directly linked to Willy.