Peeling Back the Layers

Kol Nidre is an annulment of vows, something that could have been said on any day of the year, yet Chazal placed it at the very start of Yom Kippur. Why there? The Torah says Lot moved to Sodom for his crops, while Rashi gives a very different reason, and the gap between the two leads straight back to Kol Nidre. Rav Elchanan Wasserman travels to America to raise money for his yeshiva and visits a childhood friend about a loose button on his suit. What was he really doing there?