It is understandable to have a holiday to commemorate leaving Egypt and becoming a nation and accepting the Torah which is what guides us daily as we do on Pesach and Shavuot but why do we have a holiday commemorating a miracle in the Midbar which doesn't seem to have a lasting effect? And why do we commemorate the ענני הכבוד more than the well of Miriam, mannah, or other miracles?
We celebrate that even as we are on the journey, we are going through a Midbar, still G-d is looking out for us to make life pleasant. For the majority of the time Klal Yisrael has been in golus on a journey. בסכת תשבו שבעת ימים כל האזרח בישראל ישבו בסכת למען ידעו דרתיכם כי בסכות הושבתי את בני ישראל, the first two times סכת is spelled without a ו, the third time with a ו. My wife's uncle says that it may allude to the three Batei Mikdash. The first two didn't last, it is only the third one last will last. On Sukkot we celebrate the journey to get to the geulah. Throughout the long trip G-d doesn't merely give us the necessities of food and water but He gives us ענני הכבוד to smooth out the path. He makes life pleasant.
Rashi (Berashis 37:25) says that the caravan carrying Yosef down to Egypt was carrying sweet spices so he wouldnt have to smell bad smells. How does this help the traumatic experience Yosef is going through? Rav Chayim Shmulevitch explains this was Hashem's way of informing Yosef, even though things look bad, I'm still here with you. Sukkot serves as a reminder that even though the golus has had errible times, Hashem is still with us, He is guiding us to the סוכות שלם.
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