The main expression we have of living in the sukkah is eating there. The factors that require one to eat in a sukkah are based on the idea that we are to consider the sukkah our main residence during the 7/8 days of Sukkos. Hence, eating events that would usually occur in your dining room during the rest of the year, should take place in the sukkah during Sukkos. Formal meals in the sukkah, but snacks on the run -- just as during the rest of the year you snack all over the place -- so, too, during Sukkos can be eaten outside of the Sukkah. Just as you would leave your dining room if there were, Chas v'Shalom, a leak in the ceiling; so, too, you can leave your sukkah because of rain.
But what if you want to stay in the sukkah? You worked so hard on it, and it's only once a year, and you have pictures and decorations that tell the story of your last 30 years in Chicago... I mean... it's geshmack to be in the sukkah. Even the whining about the cold and the bees is part of the charm. On that issue specifically, there are two simanim in Shulchan Aruch, Orach Chayim, Siman תרלט/639 that seem to be at odds with each other. In syef 2 (in the middle; it's long, but right at the top of קד/104 in the new Dirshu edition of Mishna Brura) says that a person who is stringent to not even drink water outside of the sukkah is praiseworthy. On the other hand, in syef 7 (again in the middle; it's long, but right at the top of קו/106 in the new Dirshu edition of Mishna Brura), says that anyone who is exempt from sukkah and does not leave there, does not receive any reward; he is nothing by a הדיוט/simpleton. (Simpleton is the nicest translation.)
So what is it? Praiseworthy or worthless foolishness? I heard a shiur on this over the Sukkos with lots of wonderful stories and sources. Then, while researching this TftD, I found that the Biur Halacha (right there on page קו/106 in the new Dirshu edition of Mishna Brura) summarizes the idea in a few words. Of course it is praiseworthy to try and get more sukkah time. When are you called a הדיוט/simpleton for your efforts? When there are other factors that push back. Such as our case, where one is exempt because of צער/anguish. Why? Because a הצטער is profaning Yom Tov, which he is required to honor! That is, the moniker of הדיוט/simpleton is applied to someone who has such a narrow view of his actions, that he doesn't see that by sitting in the sukkah -- from which he is exempt -- is actively profaning the Yom Tov itself with his anguish.
To be very blunt (as you likely know, I only have two ways of speaking -- blunt and very blunt): this הדיוט/simpleton has a disagreement with HaShem about what is important. HaShem says that you are exempt from sukkah, but still required to honor and rejoice in the Yom Tov. This הדיוט/simpleton, on the other hand, feels that sukkah is really the important thing. "Don't worry, HaShem," thinks the הדיוט/simpleton, "I got this."
This idea comes up in Nedarim (59a, 22a): R' Nosson says that anyone who makes a neder, it is as if he built a (forbidden) altar; anyone who fulfills -- that is, does not ask to be released from the vow -- is as if he has actually brought offerings on that altar. The Ran (22a) explains that this person has seen there are a lot of forbidden things in the Torah, so he decides that HaShem must want us to refrain from pleasures of this world and decides to help HaShem out by heaping more prohibitions on himself. It is the same principle. HaShem wants Jews to fulfill the entire Torah. This הדיוט/simpleton, on the other hand, feels that prohibitions are really the important things. "Don't worry, HaShem," thinks the הדיוט/simpleton, "I got this."
I expressed the core of this thought in a TftD almost a decade ago: Evil Begins with Simple Solutions and Simple Solutions are the Beginning of Evil. It is nice to have a more solid foundation. In other words, it is nice to discover that my inkling might even be true!
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