From a philosophical perspective, why would Sai Baba intentionally lead a devotee like Kashiram into debt and poverty?

The financial ruin of Kashiram was not a punishment but a profound spiritual lesson orchestrated by Sai Baba. Chapter 0 clarifies that Kashiram had developed an intense attachment and pride related to his ability to give Dakshina to Maharaj. He would feel deeply hurt on days Baba did not take money from him. This feeling, the text explains, is an obstacle to spiritual progress because pride creeps in. To remove this spiritual impediment, Baba's leela was to dismantle the foundation of that pride. By relentlessly demanding Dakshina while Kashiram's finances dwindled, Baba forced him to confront the illusion of being a 'giver.' The ultimate goal, as described in Chapter 0, was for Kashiram to realize he did not have the power to give, thus purifying his devotion and clearing his spiritual path.