Why did Maharaj cause Kashiram to face financial difficulties?

Maharaj's actions towards Kashiram were a leela designed to remove an obstacle to his spiritual progress. As described in Chapter 0, Kashiram felt great pride in his ability to give Dakshina to Maharaj. This pride is considered an obstacle on the spiritual path. To remove this pride, Maharaj first started demanding Dakshina from him relentlessly, even after Kashiram's money ran out. He instructed Kashiram to borrow money, which continued until the lender refused. This entire process was orchestrated to make Kashiram realize he did not truly have the power to give, thereby purifying his devotion and helping his spiritual advancement.