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.
Tonight R' Frand analyzed a portion of the donkey's conversation with Bilaam from two perspectives. The Torah writes in Bamidbar 22:28 that the donkey asked Bilaam why it struck her "Shalosh Regalim." The use of the word regel is curious as the more common expression would have been "pa'amim" or times.
Rashi is bothered by this question and he explains that the donkey was telling Bilaam that he had no chance to defeat the Jews will be going up to be Oleh Regel three times a year.
However Rashi's explanation only raises an additional question --- of all of the mitzvos in the Torah, why did the donkey choose this as proof of the Jews connection to Hashem. Other mitzvos such as Kabbalas Ol Malchus Shamayim or the Tamid sacrifice would seem suggest a stronger bond with Hashem!
R' Frand first answered the question by quoting the Sfas Emes who explains that the mitzva of Oleh Regel shows the connection of the Jews to Hashem. The same way that the Jews are Hashem's chosen people, the land of Israel is the location that Hashem has chosen to be the unique home of the Jewish people and no other land can be a substitute for it. This is a simple law like the law of nature. The donkey is in effect telling Bilaam that much like gravity requires the ball which is dropped to fall to the floor, so too the Jews as the chosen nation are tied to the land which Hashem has chosen for them and you cannot defy this law.
In the end Bilaam accepts this by stating in Bamidbar 23:9 "Ki MeiRosh Tzurim..." Rashi explains this pasuk as making reference to the Avos. But the Sfas Emes sees as proof of Bilaam heeding the words of the donkey as he is saying, the same way that I see the hills and mountains in Israel, I see that the Jews belong there and I have no chance to prevent it.
R' Frand also gave a second approach to the words of the donkey. He quoted a Gemara in Chagigga which states that people with three types of jobs were exempt from being oleh regel - the tanner, the coppersmith and the dung cleaner. The reason they are exempt is because all males are supposed to be in attendance and these people who have jobs which cause them to become particularly pungent will cause others to not to want to be near them.
R' Frand next quoted a Medrash in Yalkut Shimoni which states on the pasuk that Jerusalem is like a city "Shechubrah La Yachdav" that there is a unique achdus when the Jews are oleh regel. While during the rest of the year a person who is makpid not to eat chullin which is tamei, during the time that the Jews are oleh regel, all the vessels are deemed to be tahor and everyone can eat together...even though immediately after the holiday ends those self same vessels need to be purified. Why? Because the Rabbis wanted everyone to be together and feel the achdus during the holidays.
This is why the donkey refers to the regalim, because he wants Bilaam to understand that he cannot beat the Jews when they have achdus.
R' Frand closed the vort by quoting the Vishnitz Rebbi who cites to Bamidbar 23:13 where Bilaam attempts to limit his view to a portion of the Jews. Why would Bilaam think he could defeat the Jews if he only attempted to impact a portion of them? He answers that Bilaam thought that if he could influence a small group of Jews to rebel and complain then perhaps he could break the achus and defeat them.
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