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.
R' Frand began by quoting Bamidbar 2 which discusses the flags and the configuration of marching. It begins with 2:3 which introduces Yehuda - וְהַֽחֹנִים֙ קֵ֣דְמָה מִזְרָ֔חָה דֶּ֛גֶל מַֽחֲנֵ֥ה יְהוּדָ֖ה . After this, Yissachar is introduced in 2:5 as וְהַֽחֹנִ֥ים עָלָ֖יו מַטֵּ֣ה יִשָּׂשכָ֑ר. However when it comes to Zevulun in 2:7, the Torah merely writes - מַטֵּ֖ה זְבוּלֻ֑ן וְנָשִׂיא֙ לִבְנֵ֣י זְבוּלֻ֔ן אֱלִיאָ֖ב בֶּן־חֵלֹֽן. The Ba'al HaTurim explains that it is written this way, even without a Vuv drawing them together, because Zevulun supported Yissachar. Zevulun was in business and Yissachar learned and the Torah did not want to treat Zevulun as lesser or just an add on. Therefore its not written as a Vuv - an and. Instead they are like one tribe together.
R' Frand quoted the Sefer Kol Dodi from R' Dovid Feinstein who asked - how did Zevulun make his money? The flag of Zevulun had a flag with a ship on it, because Zevulun made his money as a merchant on the sea. He explained that this is not the safest way to make a living, but the tribe did not choose a safer way of earning a living. Why? Because this had a tie to Hashem, they knew that it was not safe and they relied on Hashem to safely guide them through. This also allowed them to part with their money for Tzedakah much more freely. When a person thinks that their money comes from their own efforts ("my hard earned money") they are not apt to give it away. But when a person sees that Hashem protects him on the seas, he is more willing to follow the command to give Tzedakah.
R' Frand also said a second vort from the Ramban who noted that the tribe of Levi was much smaller than the others, even though Levi was quoted from one month old instead of 20 years old. Why were they fewer in number? The Ramban explains that this supports the Chazal that the more the Egyptians oppressed the Jews, the Jews were more fertile and multiplied. Since the Tribe of Levi was not enslaved, they did not have the bracha of fruitfulness - six children being born at a time.
R' Frand said that the lesson from this is the Yiddish expression (translated to English) - man thinks and Hashem laughs. R' Frand quoted the Sefer Be'er Yosef who states that the plague of blood came on the Egyptians because they did not allow the Jewish women to go to mikva - blood vs blood. What Pharaoh did not know is that when women are stressed and in a difficult situation, they sometimes stop seeing niddah blood and then don't have to go to mikva. Thus the other tribes could continue to be together, but the tribe of Levi was not stressed and the women did see niddah blood, but they still could not go to mikva. Again man thinks and Hashem laughs. And another reason that Levi was smaller in number.
R' Frand also noted that R' Chatzkel Levenstien observed that the tribe of Dan was the second largest tribe, even though Dan only had one child when he went to Egypt. Meanwhile, the tribe of Binyamin had ten sons. Again, man thinks, but Hashem laughs at man's calculations.
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