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.
Yes, certainly Willie is driven by a transcendental goal similar to that of Weber’s workers in a class setting where mobilization between classes is unrestricted economically or socially. Now what I don’t believe is that Willie’s drive was irrational in the beginning of his career and the start of his family, as he seeks to acquire those things (tangible and intangible) that distinguish him a part of a certain social and economic class order. Weber states in his Fundamentals Concepts of Sociology, “that when market conditions prevail (eg, capitalism), property and lack of property are the basic categories of all class situations” and Willie’s drive in relationship to Max Weber’s workers in a capitalistic economy becomes irrational as Willie’s actual economic position or profit goal does not match the realistic economic goal of Weber’s capitalistic society that denotes an upward mobility of class and therefore Willie’s drive, as he struggles to maintain his economic profit and social grasp, begins to spin out of control causing him to become delusional and irrational in his hopes of finally achieving the brass ring of the symbols of success within a capitalistic economy.