I have my own strong preferences and doubts. How does Sai Baba's interaction with Dharamsee show he handles such issues?

The account in Chapter 35 directly addresses this situation. Boss Dharamsee had a strong aversion to grapes with seeds and was also worried about eating them unwashed due to a doctor's orders. His mind was filled with these problems when Baba offered him the grapes. He even felt it was difficult to eat them. However, Baba knew his internal state and his thoughts. Instead of conforming to Dharamsee's preference, Baba challenged it by giving him more grapes and commanding him to eat. When Dharamsee surrendered his preference and obeyed, he was rewarded with a miracle: the grapes became seedless. This shows that while Baba is aware of our preferences and doubts, surrendering them and trusting in his wisdom can lead to transformative experiences where those very issues are miraculously resolved.