Why does a wealthy person have to sit for a week in a temporary dwelling?
Precisely after the harvest has been gathered, the Torah sends a person into a sukkah. Jewish thinkers saw the Festival of Ingathering as a confrontation with the spiritual danger that can arise from abundance.
The problem with money is not money. The problem is what money can whisper to its owner: you are protected, independent, more important. Modern culture adds another layer: possessions have become a language of identity. Which car, which neighborhood, which brand, which vacation. A person does not merely buy an object; he buys a story about who he is.
For one week the sukkah places the wealthy and the simple person under s’chach. Not to erase economic differences, but to remind us that a person’s net worth in the bank is not the worth of the person.
Money can buy a larger house, but it cannot enlarge the person living inside it. The question is not only how much we accumulated, but whether, as our possessions grew, the human being within us grew as well.