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Shemini Atzeret and the Sukkah - Beyond the Shulchan Aruch
ההלל והשמחה שמונה כיצד מלמד שאדם חייב בכבוד י"ט האחרון של חג כשאר כל ימות החג סוכה שבעה כיצד גמר מלוכל לא יתיר את סוכתו אבל מוריד הוא את הכלים מן המנחה ולמעלן בשביל כבוד י"ט האחרון
The Hallel and the celebratory shelamim sacrifice are observed for eight days. What is the significance of this statement? It teaches that we are obligated to honor the final day of the Festival in the same manner as the other days of the Festival. The Festival of Sukkot (is observed) for seven days - in what manner? A person should not dismantle his Sukkah but should remove the (eating and drinking) vessels from his Sukkah on the afternoon of the seventh day in honor of the last day of the Festival.
ר' אבא בר כהנא ר' חייה בר אשי בשם רב צריך אדם לפסול סוכתו
מבעוד יום ר"י בן לוי אמר צריך לקדש בתוך ביתו. ר' יעקב בר אחא בשם שמואל קידש בבית זה ונמלך לוכל בבית אחר מקדש. רבי אחא רבי חיננא בשם רב מי שסוכתו ערבה עליו מקדש בלילי יום טוב האחרון בתוך ביתו ועולה ואוכל בתוך סוכתו. א"ר אבין ולא פליגין מה דאמ' רב בשלא היה בדעתו לוכל בבית אחר מה דאמר שמואל כשהיה בדעתו לוכל בבית אחר. אמרה מנא אתיא דשמואל כר' חייה ודר' הושעיה כר"י בן לוי א"ר אימי זאת אומרת שהן נחלקין בפירוש
Rabbi Abba bar Kahana and R. Chiya bar Ashi said in the name of Rav, "A person needs to dismantle his sukkah in the afternoon of the seventh day of the Festival."
R. Yehoshua ben Levi said, "He must recite Kiddush (on the night of Shemini Atzeret) in his home."
R. Ya'akov bar Acha said in the name of Shmuel, "If he recited Kiddush in one home, and then decided to eat his Festival meal in another location, he should recite Kiddush a second time."
R. Acha bar Chinna said in the name of Rav, "One who finds eating in his sukkah pleasant should recite the Kiddush within his home, then enter the sukkah and eat his meal there (on the night of Shemini Atzeret)."
R. Avin stated, "There is no dispute between the views of Rav and Shmuel, because Rav refers to a case in which his intention was not to eat in another house/place, while Shmuel's view refers to a case in which his intention was to eat in another house/place."
R. Mana said, "The view of Shmuel is the same as that of R. Chiya (bar Ashi, above - namely, that he needs to fully dismantle his sukkah, and recite kiddush and eat in his home), while R. Hoshaya (who stated that making kiddush at home was sufficient to allow eating in the sukkah) follows the opinion of R. Yehoshua ben Levi."
R. Ami said, "This (statement of R. Mana) shows that Rav and Shmuel disagreed in their views." (contra R. Avin above)
Numb. 29:35:) “On the eighth day [you shall have] a solemn assembly.” Let our master instruct us: Is it permitted to eat outside the sukkah on the Feast (of Tabernacles)?39BB 75a; ySuk. 2:7 (23a); Suk. 27ab.
Thus have our masters taught (in Suk. 2:6): R. Eliezer says, “One is obligated to eat fourteen meals in the sukkah, one [each] day and one [each] night.” But the sages say, “There is no prescribed number except [only] on the night of the [first] festal day [of the feast].”
But why did the sages permit one to be freed from the sukkah on the last festal day? Simply because the whole seven days of the festival they had prayed for abundant dew, while on the last day they prayed for rain. They therefore were freed from the sukkah, so that they might pray wholeheartedly for rain.
Nevertheless the last day of the holiday is reckoned as belonging to the days of the festival. Why? Because it is so written (in Numb. 29:35), “[On the eighth day] you shall have a solemn assembly (atseret).” Now it was fitting for it to come fifty days after the festival, just as Pentecost (Atseret) comes fifty days after Passover; but the Holy One, blessed be He, said, “It is winter and they will not be able to leave their houses to come here [to Jerusalem].40Cant. R. 7:2:2; PRK 28:7.

​​​​​​​ Rather let them make the solemn assembly while they are [already here] with Me.” How is it shown? From what they read on the matter (in Numb. 29:35), “On the eighth day [you shall] have a solemn assembly.”
וְאָמַר רַבִּי אַבָּא בַּר זַבְדָּא אָמַר רַב: אָבֵל חַיָּיב בַּסּוּכָּה. פְּשִׁיטָא? מַהוּ דְּתֵימָא: הוֹאִיל וְאָמַר רַבִּי אַבָּא בַּר זַבְדָּא אָמַר רַב: מִצְטַעֵר פָּטוּר מִן הַסּוּכָּה — הַאי נָמֵי מִצְטַעֵר הוּא, קָמַשְׁמַע לַן: הָנֵי מִילֵּי צַעֲרָא דְמִמֵּילָא, אֲבָל הָכָא, אִיהוּ הוּא דְּקָא מְצַעַר נַפְשֵׁיהּ, אִיבְּעִי לֵיהּ לְיַתּוֹבֵי דַּעְתֵּיהּ.
On a similar note, Rabbi Abba bar Zavda said that Rav said: A mourner is obligated in the mitzva of sukka. The Gemara asks: That is obvious; why would he be exempt? The Gemara answers: Lest you say that since Rabbi Abba bar Zavda said that Rav said that one who is suffering due to his presence in the sukka is exempt from the mitzva of sukka, one could have said that this mourner too is one who is suffering and should be exempt as well. Therefore, he teaches us that the mourner is obligated in the mitzva of sukka. These cases are not similar, since this exemption from sukka applies only with regard to suffering that is caused by the sukka itself, e.g., when one is cold or hot or when the roofing has a foul odor. However, here, in the case of a mourner, where he is causing himself to suffer unrelated to his presence in the sukka, he is required to settle himself and fulfill the mitzva.

Questions for Discussion

(1) The Shulchan Aruch states that one should eat in the sukkah on Shmini Atzeret (OH 668:6) as does Rambam (Hilchot Sukkah 6:14). This avoids certain problems (making kiddush in the house but eating in the sukkah) but creates others (eating in the sukkah, but without a blessing). Do you think the approach of the above sources is more or less sensible than the Shulchan Aruch's/Rambam's? What problems do the above sources mitigate, and what problems do they conversely create?

(2) Among Jews, customs vary with regard to eating the sukkah on Shmini Atzeret. Are these sources, in your view, sufficiently clear and authoritative to act in a manner other than that of the Shulchan Aruch/Rambam? What other factors come into play when deciding upon a specific approach to this issue?

(3) In Israel, there is on question whatsoever that we do not eat in the Sukkah on Shmini Atzeret (which is also Simchat Torah). With the state of Israel now the largest Jewish population center in the world, and poised to become home to the majority of world Jewry in the near future, what would the benefits be of adopting a single day of Yom Tov? What would be the drawbacks?