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Can one intentionally wait for a "painful" situation to be exempt from Sukkah?

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The Gemara states (Sukkah 26a.9 et. al.):

מצטער פטור מן הסוכה

One who is in pain is exempt from Sukkah

This is codified as halacha in Shulchan Aruch, Orach Chaim 640:4.

Suppose it's going to pour later, and as such one would be exempt from Sukkah. Can one intentionally delay his meal, such that when he eats it will be raining and he may eat inside, or would this be a violation of the positive commandment to eat in a Sukkah? Does it make a difference if it's the first night or a later point on the holiday?

As always, CYLOR if this is relevant for you.

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You're asking your question in a very specific way, but it can be generalized to be: "Is it permissible to find ways to avoid fulfilling a mitzvah?. If it's forbidden, is it considered nullifying the positive mitzvah that was avoided?".

Rav Asher Weiss in Minchas Asher Bamidbar § 17, found online at his site here, has an article about the inverse question: Does a person have to go out of their way to become obligated in a mitzvah.

The article is specifically addressing the idea of the Pesach offering. The Torah says that someone who is too far away from the Temple is exempt, and waits for Pesach Sheni. What if someone is far away, and has time to make it to the Temple if they travel. Are they obligated to do so? First, he writes the following:

אם יש חיוב להתקרב ואם אינו מתקרב עובר באיסור הרי בודאי אסור לו להתרחק

If a person is obligated to travel to the Temple, and by not doing so they're transgressing, it for sure would then be forbidden to distance oneself.

So, in this case, he says it's forbidden to make oneself exempt. That is however, if it's a transgression to avoid the mitzvah.

He brings a dispute in this. The Tzelach Pesachim 3b seems to have no problem if someone doesn't travel to the Temple. Whereas the Minchas Chinuch § 5 says a person is definitely obligated to travel to the Temple to obligate oneself.

He then analyzes the Tzelach's opinion. He suggests that the Tzelach agrees a person is obligated to make sure they can fulfill a mitzvah, and avoid any situation which would make themselves exempt. For example, a person has to build a sukkah or purchase the four species, and can't wait until Sukkos comes and say "I don't have, what can I do". With regards to Pesach, since they are already in a state of being exempt (since they're far from the Temple, which the Torah explicitly exempts), they don't have to obligate themselves.

ואף שחייב אדם להשתדל בצרכי המצוה ולמנוע מצב של אונס ועיכובים מקיום המצוה כיון שהוא חייב בה אינו חייב להכניס עצמו לכלל חיוב אם הוא במצב שבו הוא פטור מן המצוה בדין תורה וזה סברא פשוטה לענ"ד

He then says something which I think more directly addresses your question.

וע"כ נראה ברור דבאמת אינו מבטל מצות עשה אם לא קירב עצמו לפני החג וכן אינו בכלל מבטל מצות עשה אם לא בנה סוכה או לא קנה לולב וכדומה ובזמן החיוב אין בידו לקיים המצוה, ורק בגוונא שבידו לקיים המצוה בזמן חיובו כגון לישב בסוכת חבירו וכן בד' מינים וכדו' נחשב מבטל מצות עשה, אלא דמ"מ נענש משום שיש חיוב כללי על האדם לחבב המצות ולהשתדל בקיומן, וחיוב זה מחייבו לדאוג לפני זמן החיוב שיהיה בידו לקיים המצוה בעידן חיובה, ואם לא עשה כן יש עליו עונש (ובאבנ"ז או"ח סימן שכ"א כתב דמושבע ועומד הוא לקיים המצוות מהר סיני עי"ש), אפילו בציצית שכל עוד אינו לבוש ד' כנפות אין עליו כלל סיבת החיוב מ"מ נענש על שלא השתדל להכנס לסיבת החיוב וק"ו כשהוא מחיוב אלא שלא השתדל להכין צרכי המצוה

Therefore, it's clear that in truth, a person doesn't nullify a positive mitzvah if they don't approach the Temple before Pesach. As well, they're not considered having nullified a mitzvah if they don't build a sukkah or don't purchase the four species, and the like, and when the time of the mitzvah comes they're not able to fulfill it. It's only in a case where it's within their ability to fulfill the mitzvah during its time of obligation. For example, they could sit in their friend's sukkah, similarly with the four species, etc. [If they don't do this], it would be considered nullifying a positive mitzvah. Nevertheless, the person will be punished, since a person has a general obligation do cherish mitzvos and to endeavor to fulfill them. This required attitude obligates them to be concerned before the time of the mitzvah arrives, such that they'll be able to fulfill it at its proper time. If they don't do this, they'll be punished (and the Avnei Neizer writes that a person is sworn from Mount Sinai to fulfill mitzvos, see there). Even tzitzis, that when a person isn't wearing a four-cornered garment they aren't obligated in the mitzvah, nevertheless they are punished for not endeavoring to make themselves obligated in the mitzvah [by wearing such a garment]. All the more so when the person is already obligated, they simply didn't make the necessary preparations.

Bottom line: If I understood his words correctly, the case you describe would not be considered a nullification of the mitzvah. However, there is a punishment for avoiding mitzvos, as the person shows they aren't interested in fulfilling them.

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