This is largely from Rav Yerucham Olshin’s ירח למואדים, סוכות, מאמר ע׳. There’s a famous מחלוקת about the meaning of the סוכה:
And in fact, the Tur decides this apparently Aggadic question as a matter of halacha:
Rav Olshin asks, of all the miracles of the wilderness, why have a holiday for this one? There were three major miracles that accompanied בני ישראל through the wilderness:
What makes this one special?
His answer starts with an apparently unrelated halacha: the laws of גמילות חסדים:
The importance of לויה comes from the Torah’s discussion of the עגלה ערופה, the ceremony when an unidentified murder victim is found:
The Maharal explains that accompanying a stranger is acknowledging that they are a human being. Offering food and water, then kicking them out, is a very poor form of גמילות חסדים.
This reminds me of Maslow’s hierarchy of needs:
The Maharal is making the point that יָדֵינוּ לֹא שָׁפְכוּ אֶת הַדָּם הַזֶּה isn’t that לויה is at the level of “Safety”; it’s at the level of “Esteem”. Someone who feels they are נברא בצלם אלקים has much less to fear.
So what were the ענני הכבוד that we commemorate with our Sukkahs? They were the expression of ה׳'s לויה:
Rav Olshin gives an amazing interpretation of ענני הכבוד. We usually translate the phrase as “the clouds of G-d’s glory”. But he says that’s backwards. The phrase means “the clouds by which G-d glorified Israel”:
And that goes with the Gra’s famous answer of the question of why Sukkot is in Tishrei:
After חטא העגל, ה׳ agreed not to destroy Israel, but would no longer accompany them into the land:
Only after that first יום כפור, the שכינה returns and ה׳ says, “I will accompany you. I will give you the לויה that says I recognize that you are all צלם אלוקים”. And that חסד is so much greater than simply offering food and water, and warrants a holiday all to itself.
Rav Olshin then turns it around, and ends with the realization that if the mitzvah of sukkah is to remember the ענני הכבוד, then that mitzvah should inspire us to not only do חסד, but to do it with כבוד הבריאות for everyone: