Why did Sai Baba force his devoted follower Kashiram into poverty by demanding so much Dakshina?

Sai Baba's actions towards Kashiram were a profound spiritual lesson, not an act of malice. As detailed in Chapter 0, Kashiram had developed a subtle pride in his ability to give Dakshina, feeling distressed if Maharaj did not accept it from him daily. This pride was an obstacle to his spiritual progress. To remove this, Maharaj orchestrated a 'Leela' by demanding Dakshina precisely when Kashiram began facing financial hardship, even making him borrow money. This experience was designed to crush his ego and make him realize that he did not have the power to give. Once he learned this lesson and his pride vanished, his financial condition improved once again.