Tonight I went with my mom and my sister to a shiur in the Great Synagogue that, happily for me, addressed this question. The shiur was given by a Rabbi Gottlieb who once attended Shaalavim and is now on sabbatical in Israel with his family. He first spoke about Sukkos and the discussion in the Gemara about what the sukkos were that B'nei Yisrael sat in in the midbar. Rabbi Eliezer said the sukkos were really the Ananei Hakavod while Rabbi Akiva said they were actual, regular sukkos. But why, asked Rabbi Gottlieb, would we have a chag to celebrate living in regular, ordinary sukkos? How can we understand Rabbi Akiva's opinion in the context of having a chag?
Rabbi Gottlieb then focused on the Shemonah Esrei that we say every day. At the end of Shemonah Esrei, we say the paragraph of Elokai Nitzor. In that paragraph, there is a pasuk (also one I have always liked) that goes, "Petach libi b'toratecha, u'vimitzvotecha tirdof nafshi." Rabbi Gottlieb pointed out that this pasuk is originally written somewhere - I think in the Gemara but I don't remember exactly - as "acharei mitzvotecha tirdof nafshi." That would be translated as, "after Your mitzvos my soul should pursue." As in, we should chase after Hashem's mitzvos. However, in Shemonah Esrei, we don't say "acharei mitzvotecha, " we say "u'vimitzvotecha." With Your mitzvos my soul shall pursue. But pursue what? Rabbi Gottlieb suggested then that what we are pursuing is God.
In the first translation, our pursuit is after mitzvos. Mitzvos, then, are the object, the goal. But the way we say it when we daven, we turn mitzvos into the method. We use mitzvos in order to chase. They become the means to pursue something higher, something greater - God.
Rabbi Gottlieb quoted from a hesped of Rav Soloveitchik where he talks about what his mother taught him (emphasis mine):
"Most of all I learned from [my mother] that Judaism expresses itself not only in formal compliance with the law but also in a living experience. She taught me that there is a flavor, a scent and warmth to the mitzvot. I learned from her the most important thing in life - to feel the presence of the Almighty and the gentle pressure of His hand resting upon my frail shoulders." - A Tribute to the Rebbitzen of Talne
Torah, Halacha, Mitzvos - they are all important. But partnered with them needs to be a quest to become close to God. One should not go around performing mitzvos in order to have a collection of them, but one should do mitzvos because through Torah and mitzvos one can enrich his relationship with God.
This, said Rabbi Gottlieb, is how one can understand Rabbi Akiva's opinion. The sukkos can be regular, ordinary sukkos and still be worthy of having a chag about them. Grand miracles are great - we celebrate them on Pesach. But Sukkos is the holiday of our every day relationship with God. It is not about extraordinary gifts. It's about the ordinary gifts we receive from God every day. It's about our simple closeness to God.
I remember learning when I was younger that we have Shemini Atzeres because God wanted us to stay a day longer with Him on this chag. This idea fits in beautifully with everything I just wrote about. If we work on becoming close to God, if we use Torah and mitzvos in order to enhance our relationship with God, then God will also be close to us, we will merit to feel "the gentle pressure of His hand" resting upon our shoulders, and God will want us to stay with Him.
We can't forget that everything we do in Judaism is for this ultimate goal - becoming closer to God. If we keep this in mind, hopefully all the other nonsense everyone worries about (you know what I mean) will dissipate. Don't you see how that stuff doesn't matter? We're not in this religion to impress anyone or to be holier-than-thou. We're not in it to collect chumras or to show off our mitzvos - as wonderful as they are - to anyone else. We're in it because we are God's people and, as God's chosen nation, the one relationship we ought to worry about most is our relationship with God. Every time we make a choice, we should remember that we are part of God's nation. How should one with a relationship with God behave?
And another thing. The simple nature of our relationship with God that we celebrate on Sukkos is such a beautiful thing to celebrate. It is on this chag specifically that we have an added day, a Shemini Atzeres, because God did not want us to leave Him. Not on Pesach when we celebrate the great miracles God performed for us. Not on Shavuos when we celebrate receiving the Torah. No. Only on Sukkos, when we celebrate our simple, every day relationship with God. The simplicity, the ordinariness is what enriches the relationship. Not the majestic nissim and niflaos. To me, this is a model of all relationships we have. Family, friends - the best moments are the most simple ones, aren't they? Not the big parties. I'm talking about the times when you go for a walk or stay up late talking or read together in the same room and don't even talk. The times when you drink hot chocolate together or get ice cream in the middle of the night or get really silly for no reason at all except for the fact that you're with someone you feel comfortable enough to be really silly around.
We have to work at these relationships - karov Hashem l'chol kor'av. God is close to those who call Him. Relationships take work, they take initiative, they take thoughtfulness, sensitivity, and sincerity. But the kind of work they require is not anything elaborate. It's the simple every day stuff. It's the ordinary times people spend together that are the strongest treasures.