From this point of view, the festival of Sukkos is utterly unintelligible. It's all about being happy - it includes a special mitzvah to constantly be happy for 7 days and it is called the "time of our happiness." But instead of rewarding ourselves with a luxury vacation or reminiscing on the good times when we were settled in our land or something like that, we build frail huts and live in them for 7 days and remember wondering in the desert. All of the eating and drinking and family time is not the central Mitzvah of the holiday, only living in a sukkah and shaking a "Lulav". It even says the festival of Sukkos lands at the beginning of winter as opposed to spring just to clarify that we're not doing it to enjoy the weather (even though originally the Jews actually started living in Sukkos in spring, when they left Egypt).
Happiness, which is called "Simcha" שמחה in the Holy Tongue, is the experience of something called שלימות, or completion. You can have a limited kind of Simcha in any completion of a goal, but real inner Simcha is in the completion of your purpose for living. You have to know the purpose of being Jewish is very big. Because there is no end to a Jew's potential your completion is by definition outside of yourself. You cannot reach it. But what you can do is much greater. You can be a dreamer. You can set yourself up to be in a state of going beyond your nature and reaching for your purpose. And if you do that, the process becomes just as special as the end goal.
That is what Sukkos is. It's not our right to just have happiness, it's our job and privilege to pursue completion and recognize how our heart finds happiness in that. Wandering the desert for 40 years was no piece of cake, even with miraculous protection. We could never get comfortable, ready to move at a moments notice to be with the divine presence. Encampments spanned everywhere from years to just days. The Mitzvos of Sukkos in all their halachic detail imprint on the subconscious of the Jewish soul the need to avoid being lazy and stagnant in order to jump on opportunities for completion as soon as they arise. And in that mode, you can realize happiness is not a carrot on a stick. Happiness is there in your heart when you notice the crazy stuff you do for a higher purpose.
("מהר"ל ע"ז דף ג; ספר החינוך; ר' ירוחם ,שיבבי דעת "עליון שמתה מעונך)