One of the major obstacles that faces modern students who encounter the philosophies of Benjamin found in Illuminations is that there are radical differences between his assumptions about reality and modern opinion. Also, there is no denying the influence of Jewish mysticism in Benjamin's writing and point of view, an influence that mattered all the more because of his station in history: he was a Jew who fled Germany during the rise of Hitler's Nazi regime.
Much of the essays point to the use of art and literature as a means of social discourse, and he spends essays unpacking short stories and novels by Proust and Kafka. There is a question to answer about what his encounter with those stories might have been like. From the comfort of modern civilization, perhaps it is less likely for readers to see the absolute cosmic horror in Kafka that Benjamin sees. A fuller examination of Benjamin's experience of Kafka would need to discuss the idea of apocalypse, because Benjamin is clearly concerned with doom in the social sphere.
Looking back on Benjamin's legacy as a thinker and writer, one might notice the irony of his point of view in history, because he died in 1940, attempting to escape the Nazis who wanted to capture him and put him in a concentration camp. His ideas should be viewed with that painful reality in mind, because his point of view is informed by the kind of horror that most humans never encounter. He writes about human life from the position of one who suspects that death might be around the corner.
