Why did Maharaj start demanding so much Dakshina from Kashiram, even forcing him to borrow money?

Maharaj started demanding excessive Dakshina from Kashiram to address an obstacle on his spiritual path: pride. As detailed in Chapter 0, Kashiram took pride in his ability to give Dakshina and would feel hurt if Maharaj did not accept it, which revealed a sense of 'I have the power to give.' To remove this pride, Maharaj began a 'barrage of demanding Dakshina' until Kashiram's money was finished. Maharaj even instructed him to borrow from a grocer. This entire leela was designed to make Kashiram realize he did not truly have the power to give, thereby humbling him. Once this lesson was learned, his pride vanished and his financial condition improved.