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 the vort tonight by quoting Rashi who stated that each of the flags of the tribes had a specific color and that the color was the same as that tribe's stone on the Urim V'Tumim.
R' Frand then quoted a Medrash which states that Hashem showed a great love for the Jews in giving them flags. This can be seen in the pasuk in Shir HaShirim 2:4 - הֱבִיאַ֨נִי֙ אֶל־בֵּ֣ית הַיָּ֔יִן וְדִגְל֥וֹ עָלַ֖י אַֽהֲבָֽה. The Medrash continues - when Hashem came down on Har Sinai accompanied by the angels, each of the 2.2 million angels had their own flag. The Jews desired these flags and Hashem said that He would provide for them and He instructed Moshe that the Jews should have a flag for each tribe.
R' Frand asked - why at the time of Matan Torah did the Jews have a desire for flags? He gave a modern day example - if your team wins the Super Bowl and they have a parade, do you want to be in a picture with one of the athletes, or the float that carries him?
R' Frand answered his question by quoting the Nesivos Shalom who explains that the Jews did not simply want the flags. Instead they saw that each of the 2.2 million angels had a flag which identified his role and the Jews wanted to flags which showed their tafkid as well. Hashem granted this request as each tribe's flag identified their nature. The flag of Reuven had the duda'im, because of his middah of chessed in procuring them for his mother when she felt bereft. The flag of Shimon was Shechem because it showed his placing his sister's honor above all.
Each of the Jews wanted a flag so that they could display their role in Bnei Yisrael.
R' Frand also discussed the tribes and the configuration they marched in - specifically the tribes of Dan, Naphtali and Asher. The Torah writes in Bamidbar 2:27 that the Nasi of Asher who traveled with Dan was פַּגְעִיאֵ֖ל בֶּן־עָכְרָֽן. This is an odd name as עָכְרָֽן means perverter. Similarly, Bamidbar 2:29 states that the Nasi of Naftali was אֲחִירַ֖ע בֶּן־עֵינָֽן. Would anyone name their child - my bad brother?
R' Frand quoted the Rabbeinu Ephraim who explains that these were not actually their given names. Instead they took on these names because they were travelling with the tribe of Dan who had taken the idol Pesel Micha with them when they left Egypt and were carrying it with them in the desert. The other tribes who were travelling with them did not want to become complacent or used to seeing an idol, so the Nesi'im took on those names to remember that their brother was doing wrong.
R' Frand closed the vort by discussing the story of Palti Ben Laish and referring to a shmuze of R' Chaim Shmulevitz. He noted that the story as told in Nach was that Palti put a sword between the beds and said that whomever crosses this will be stabbed. But since he was the one who put the sword, couldn't he have removed it as well?
R' Chaim explained that Palti felt a sense of terror the first night as he knew that she was a married woman, notwithstanding Shaul's machinations. In order to not forget how he felt, he put the sword between them as a constant reminder.
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