I heard Damu Anna was childless. How did Sai Baba help him with his family situation?

Yes, the source material confirms that Damu Anna faced this personal difficulty. Chapter 25 of the Shri Sai Satcharitra explains that while Damu Anna was a well-to-do person and had two wives, he had no children. This part of his story is used to illustrate how Sai Baba intervenes to remove the suffering of his followers. The text explicitly states, "By receiving Sai's blessings, he was blessed with sons." This event is presented as a direct result of Sai's grace and a testament to the belief that when one-pointed faith is established, Sai wards off misfortunes and grants the desired objects to His devotees, highlighting the Guru-Mother's role as an "Ocean of Mercy."