The following is a brief summary of some of thoughts said over by R' Frand on the parsha this evening. I have attempted to reproduce these vorts to the best of my ability. Any perceived inconsistency is the result of my efforts to transcribe the shiur and should not be attributed to R' Frand.
In Bamidbar 9:1-15 the Torah discusses the laws of and the story involving Pesach Sheni. The first pasuk of the perek tells us that this topic arose in the first month of the second year after the Jews left Egypt. However, Sefer Bamidbar begins in the second month of the second year, thus later than this story.
Rashi comments on this phenomenon and states that this is an example of the rule of Ein Mukdam U'M'uchar BaTorah - there is no later or earlier in the Torah. He further explains that the reason that the stories appear "out of order" is that the Pesach Sheni was the one and only time that the Jews offered the Korban Pesach in the desert and it was an embarrassment for them. As such, Hashem did not want to begin Sefer Bamidbar with this story.
R' Frand then asked, why was this so significant that it warranted being moved back in the sefer? The failure to offer the Korban Pesach was due to many of the Jews being incapable of undergoing bris millah due to the travel and conditions in the desert. This was not a voluntary neglect of a mitzva.
R' Frand answered the question by quoting the Shalal Rav who cited a vort and story involving R' Chaim Shmulevitz. When Yosef was sold down to Egypt, he was transported via a caravan of Ishmaelites who were carrying spices. This was atypical as they usually transported oils, but Hashem looked out for Yosef and arranged that his transport had pleasant smelling spices.
But why would that make a difference to Yosef? He was at his nadir, having been sold down to Egypt by his brothers. Why would he care if the truck smelled like oil or spices?
R' Chaim answered that it probably would not have made a difference to Yosef, but Hashem wanted to show Yosef that even though Yosef was being sold to Egypt as part of His plan, Hashem still cared about Yosef and wanted him to be comfortable on the journey.
Similarly, although the Jews did not offer the Korban Pesach after year 2, Hashem did not want this story to be front and center in the beginning of Sefer Bamidbar. The rationale for not offering the Korban Pesach could not be changed, but Hashem wanted to show the Jews that He cares about their feelings and moved the story to later in the Sefer.
R' Frand closed the vort by quoting R' Bukspan who told a story about R' Twerski. When he was young and living in Milwaukee, his home was the place where mishulachim stayed when they were in town. One year there was a meshulach who stayed with them for Rosh Hashanah. In the afternoon, R' Twerski's father called him in and asked - were you playing chess? Yes, the boy replied. But its Rosh Hashanah! The boy said - the Meshulach told me it was OK. R' Twerski's father showed his displeasure, but after a moment he asked - did you get checkmate? Yes, the boy replied. His father replied - good. Because even though the father needed to rebuke him for playing chess on Rosh Hashanah, he also needed to show that he cared.
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