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Is the blessing of Leisheiv Basukkah said before or after the blessing over food?
From the letter of the law, it would be deemed proper for the blessing of Leisheiv Basukkah to be recited prior to the blessing of Hamotzi [or Mezonos]. Nevertheless, the [widespread] custom [of all communities in previous times] was to only say the blessing of Leishev Bassukah after reciting the blessing of Hamotzi [or Mezonos]. [Practically, the widespread Sephardi custom of today is like the former approach, to recite the blessing of Leishev Bassukah while standing, and only then recite the blessing over the food while sitting. However, the Ashkenazi custom of today retains the original custom to first recite the blessing over the food and only then recite the blessing of Leishiev. Thus, if one eats more than a Kibeitza of bread, he first says the blessing of Hamotzi and then says the blessing of Leisheiv Basukkah and then eats. Likewise, if one eats more than a Kibeitza of Mezonos, he first says the blessing of Mezonos end then the blessing of Leishev Basukkah and then eats the Mezonos. Nonetheless, if one first said the blessing of Leisheiv, prior to the blessing of the food, he fulfills his obligation.]
When is the blessing of Leisheiv Bassukah said during the Yom Tov/Shabbos meals? During Kiddush of the night meals of the Yom Tov of Sukkos, as well as Shabbos Chol Hamoed Sukkos, the blessing of Leishiev Basukkah is said prior to drinking the wine. However, on the 1st night of Sukkos, it is said before the blessing of Shehechiyanu, [while on the 2nd night it is said after the blessing of Shehechiyanu]. However, during the Kiddush of the day meal of the Yom Tov of Sukkos, and Shabbos Chol Hamoed Sukkos, the blessing of Leisheiv is said after the blessing of Hamotzi, and not by Kiddush. [However, some Poskim rule that even by the day meal the blessing of Leisheiv is said after the blessing of Hagafen, prior to drinking from the wine, and so is the Chabad custom.]
The Ashkenazi custom is to say the blessing of Leisheiv Bassukah after saying the blessing of the food, but prior to eating it. The Sephardi custom is to say the blessing of Leisheiv Bassukah prior to saying the blessing of the food, while standing.
 Admur 643:4; See Kaf Hachaim 643:14-20; Nitei Gavriel Sukkos 45:3
 Admur ibid; Michaber 643:3 [and so is his main opinion, as written in Beis Yosef 643]; Maharam Merothenberg in Tashbeitz 142 that so should be followed, brought in Rosh 4:3, and Tur 643; Bach 643; Mur Uketzia 643; Moed Lekol Chaiy 22:1; Yifei Laleiv 3:2; Ben Ish Chaiy Haazinu 5; Kaf Hachaim 643:16; Yalkut Yosef 643:5
The reason: As one becomes obligated in the blessing of Leishev Basukkah as soon as he sits down to eat [even prior to eating], and it is therefore proper to precede it to the blessing of Hamotzi, which is not obligatory until he decides to actually taste the food. [Admur ibid; Taz 643:4; Beis Yosef 643]
 Including Sephardic communities. [So is evident from Michaber ibid]
 Admur ibid; Michaber 643:3; Tur 643; Rosh Sukkah 4:3; Hagahas Rabbeinu Peretz in Tashbeitz ibid
The reason: The custom is to say the blessing of Leisheiv Basukkah after the blessing of Hamotzi, as the saying of the blessing of Hamotzi is the start of the meal, and the people of the world saw it fit to begin the meal prior to saying the blessing over the Sukkah, as one only recites the blessing of Leisheiv Bassukahon during a meal [and hence we first say Hamotzi and only after do we say Leisheiv]. The blessing of Leisheiv Bassukah is not considered a Hefsek/interval between the blessing of Hamotzi and the eating, being that this blessing is needed for the meal, and any matter which is needed for the meal is not considered an interval, as explained in 167:9. [Admur ibid; See M”A 643:2; Beis Yosef 643; Levush 643:3; See also Admur 190:1; 296:1; 473:6; See Kaf Hachaim 643:15]
 Yalkut Yosef ibid, following the ruling of the Beis Yosef ibid, Ben Ish Chaiy ibid, Kaf Hachaim ibid
 Pashut; Birchas Habayis Shaar 52:11; Nitei Gavriel ibid
 Admur 643:1; Michaber 643:1; Sukkah 56a
 Admur ibid; Michaber ibid; Rama 643:2
 Michaber and Rama 661:1, and so is implied from Admur 643:1
Other Opinions: Some Poskmi rule that on the second night as well the blessing of Leisheiv is to be said before the blessing of Shehechiyanu. [Bach; Rashal; Radbaz] Practically each is to follow his custom. [M”B 661:2]
 Admur 643:3; Taz 643:4; Tur 643; Shaareiy Teshuvah 643:3; Alef Hamgen 59; Birchash Habayis 52:10; Misgeres Hashulchan 135:14; opinion in M”B 643:9
The reason: Leisheiv is only said by Kiddush of night being that it contains the blessing of “Kiddush Hayom.” However, by day, being that it only contains the blessing of Hagafen, it is not said by Kiddush but rather by Hamotzi. [Admur ibid]
 Kneses Hagedola 661; Levush 660:2, brought in Beir Heiytiv 661:1; P”M 643 M.Z. 4; Mamar Mordechai 643:5; Birkeiy Yosef 643:5; Aruch Hashulchan 643:3; Kaf Hachaim 643:18; Opinion in M”B 643:9; See Nitei Gavriel 45:2
Opinion of M”B: The M”B 643:9 brings down both opinions and rules that one may choose like whom to follow.
 Sefer Haminhagim p. 67; See Otzer Minhagei Chabad 135