Why did Maharaj start demanding Dakshina from Kashiram after he had already lost his wealth?

Maharaj's actions were a deliberate Leela, or divine play, designed to remove a spiritual obstacle from Kashiram's path. According to Chapter 0, Kashiram had developed pride in his ability to give, feeling hurt if Maharaj didn't accept his Dakshina. To cure this pride, Maharaj engineered a situation where Kashiram faced financial ruin. It was precisely at this point that Maharaj began demanding Dakshina relentlessly, even telling him to borrow money. This was done to bring Kashiram to the realization that he did not truly possess the power to give, thereby dissolving his ego and helping his spiritual progress.