Note: The spelling/transliteration of Hebrew in the following is either the cited authors or, when a book is cited, my transliteration. I have tried to put Hebrew next to the “English” to help the reader better understand the author’s meaning.
Let there be light … and erub tavselin
When the first days of Sukkot fall on Thursday and Friday, one must ensure to prepare an Erub Tabshilin (עירב תבשילין) on Wednesday, before the onset of Yom Tob, to allow cooking on Friday for Shabbat.
The women’s obligation of Hadlakat Nerot (candle lighting) applies on the first two nights of Sukkot, just as on Friday night. On Wednesday night, the first night of Sukkot, the woman lights candles before sundown, at the time printed in the calendars, similar to the candle lighting on Friday afternoon, and she recites the Beracha “Le’hadlik Ner Shel Yom Tob”. (לחדלק נר ליום טוב)
On Thursday night, the second night of Yom Tob, she lights candles – with the same Beracha – when the husband returns home from the synagogue. These candles must be lit from an existing flame. On Friday afternoon, she lights Shabbat candles before sundown, from an existing flame, reciting the usual Beracha of “Le’hadlik Ner Shel Shabbat” (לחדלק נר שבת). (R. Eli Mansour http://www.dailyhalacha.com/Display.asp?ClipID=687 )
Sheheheyanu – How many times?
When constructing a Sukkah for oneself, it would be appropriate to recite the blessing of Sheheheyanu over its construction. However, we rely on the blessing of Sheheheyanu that is recited during the Qiddush (קידוש) to cover this also.
If one did not eat in the Sukkah on the first night of Sukkoth, even though one recited Sheheheyanu (שהחינו) in the house, one must recite Sheheheyanu again when eating in the Sukkah, on account of the Sukkah.
One recites the blessing of Sheheheyanu on the Sukkah the first time one eats in the Sukkah, irrespective of whether that occurs during the day, or at night. (R. Ya'aqob Menashe http://www.atorahminute.com/2013-09-16 )
If someone did say the Sheheheyanu (שהחינו) blessing when building the sukkah, the person does not say the Sheheheyanu again when sitting in the sukkah for the first time. (R. Yosef Messas, Hod Yosef Hai, Pg.179)
Who is obliged, who is optional?
Males who are bar mitzvah (13 years and a day) are obliged to sit in a sukkah.
Boy should be encouraged to join the men from age 5 or 6. (R. Ya'aqob Menashe http://www.atorahminute.com/2013-09-15 )
Although women and children are exempt from the Sukkah, however, wherever possible, they should also perform the commandment and they will get reward for it. (ibid.)
Honoring Ushpizin
The Zohar notes that a crucial part of the Ushpizin concept is bringing joy to the poor, either by inviting them to one’s Succa together with the Ushpizin, or by giving them charity in the Ushpizin’s honor. The Ushpizin derive enjoyment not from the food served in the Succa, but rather from the assistance lent to the poor, and thus besides inviting the Ushpizin into our Succa, we must also ensure to care for the needy as part of our hosting these special guests. (R. Eli Mansour http://www.dailyhalacha.com/Display.asp?PageIndex=&ClipID=2564)
First night blessings
The sequence for the recitation of Kiddush (קידוש) on the first night of Sukkot is as follows: “Boreh Peri Ha’gefen "(בורא פרי הגפן) “Baruch Ata…Asher Bahar Banu…Mekadesh Yisrael Ve’ha’zemanim” (אשר בהר בנו), “Le’sheb Ba’sukka” (לישב בסוכה), “She’hehiyanu” (שחהינו). After one recites “Shehehiyanu” everyone sits down and the Kiddush cup is passed around for everyone to drink. It is important that everyone sits in the Sukka after Kiddush, as it is through sitting that one fulfills the Misva. (R. Eli Mansour http://www.dailyhalacha.com/Display.asp?ClipID=687 )
The blessing “Le’sheb Ba’sukka” (לישב בסוכה) on erev Shabat and erev Yom Tov should be said standing as with the other blessings of the day. At other times, “Le’sheb Ba’sukka” (לישב בסוכה) should be said sitting; however, if said standing that, too, is OK. (R. Shalom Messas, ילקות שמ''ש Pg. 134)
Etrog and Lulav
While the etrog should be free from defects, it is not necessary to inspect it under a magnifying glass. (R. Yosef Messas, Hod Yosef Hai, Pg.178)
According to Maran (Yosef Caro), people lacking a lulav and etrog may participate in the circling of the bemah (להקיף הבימה). The Remah (R. Moses ben Israel Isserles of Krakow) ruled that only those with etrog and lulav may circle the bemah. The custom (מנחג) of North Africa (Morocco to Libya) follows Maran. (R. Shalom Messas, ילקות שמ''ש Pg. 137)
Intermediate days
On the intermediate days (ימי חול), “Le’sheb Ba’sukka” (לישב בסוכה) is said sitting and immediately after the blessing on the bread (המוציא) but before tasting the bread. (R. Shalom Messas, ילקות שמ''ש Pg. 135)