If Sai Baba's Guru was a perfect saint whose desires were fulfilled, why would he ask his disciple for money? Does this not seem contradictory?

Chapter 19 directly addresses this apparent contradiction. While it might seem paradoxical for a desireless saint (Purnakam) to ask for money, the text explicitly instructs the reader, 'Let no such doubt enter the mind.' It clarifies that the Guru's request for 'two paise' was not for worldly currency, as he had no use for it. The request was a test and a teaching. The 'two paise' he sought were Faith (Nishtha) and Patience (Saburi). Therefore, the act of asking was a symbolic method to elicit and confirm the disciple's commitment to these essential spiritual qualities, rather than a desire for material gain.