Can you walk me through the sequence of events from when Cholkar first arrived in Shirdi to when Baba mentioned the tea?

Certainly. As per the account in Chapter 15, when Cholkar finally arrived in Shirdi, his mind was filled with joy. The first thing he did was have Sai Baba's darshan, at which point he prostrated himself at Baba's feet in a state of supreme bliss. Immediately after, he fulfilled his long-held vow by distributing sugar and offering a coconut with a pure heart. After this, Cholkar, who was a guest of the devotee Jog, went to Jog's residence. It was at this specific moment, as Cholkar the guest was preparing to depart, that Baba spoke to Jog and gave the meaningful instruction to serve him "cups of tea, well-filled with sugar."