Kiddush on Sukkos before tzeit?

Question

The first night of Sukkos we make kiddush after tzeit (Rama 639:3). My understanding is that this is purely because of the bracha of לישב בסוכה which you can't say until it's definitely night (Magen Avraham and Biur Halacha). The Dirshu Mishna Berura quotes someone, I believe it's R' Chaim Brisker, who makes the point that we worry about the possibility (R' Tam?) that accepting Yom Tov does not create a full reality of Yom Tov that would allow you to say this bracha. Otherwise, you could make kiddush and eat, and just make sure to eat a kezayit of bread after tzeit.

My question:

Are there situations when you can make kiddush before tzeit?

• You are an woman and not eating in the sukkah, or a Sefardi woman and eating in the sukkah with no לישב בסוכה Does this allow for Kiddush to be made before nightfall?
• You're a man and will not be able to eat in the sukkah, e.g.a hurricane is building up and its pikuach nefesh if you go in after nightfull, should one recite Kiddush in the Sukkah before nightfall?
• It's pouring and it's obvious that it's going to continue all night. The Rama (639:5) says that you should make kiddush in the sukkah, so that your שהחינו will apply to it, and eat a kezayit there; the Mishna Berura says that you don't make a לישב בסוכה because many Rishonim say that you are not yotzei. Can you do this early, go inside and eat most of your meal, and then go back to the sukkah and eat another kezayit of bread?
• It's after sunset and not raining now, but it's going to start soon, before tzeit, and continue all night. If you wait, you won't have any chance to fulfill the mitzva according to the opinions that rain ruins the sukkah on the first night. Also, you won't be able to make a לישב בסוכה in any case. Should you make kiddush and eat a kezayit in the sukkah now, to at least get a chance of doing the mitzva according to those opinions, and then eat another kezayit after tzeit, to get 100% chance according to the others?

Answer 1

• A woman eating outside the Succah can make Kiddush before Tzeis (nightfall) as Kiddush a woman is Obligated to do Kiddush Mideoraita, but she is not obligated to eat in the Succah. So if she chooses to the Mitzva waiting till night to eat in the Succah she makes a brocho if ashkenazi and ommits if she is Sefardi. But neither has an obligation therefore she can do Kiddush before Tzeis outside the Succah in-order to eat if she wants.

  Shavuos 20a:נשים חייבות בקידוש היום דבר תורה דאמר קרא זכור ושמור כל שישנו בשמירה ישנו בזכירה
  Kiddushin 29a:וכל מצות עשה שהזמן גרמא אנשים חייבין ונשים פטורות

• A man however is specifically obligated to eat in the Succah on the first night so making Kiddush on wine must be done in the Succah at Tzeis (nightfall). In the case where its pouring for next few hours the best thing to do is to eat before davening if you are hungry when you are not obligated to say Kiddush yet that way your not hungry and can wait all night until a lapse in the rain then make Kiddush and Hamotzi in the Succah so you have fullfilled your obligation according to everyone and you can make a brocho leishev and Shehechianu at the same time of Kiddush like Chazal instituted. If its getting close to dawn then just do kiddush and eat a kzais in the rain like the remo (639,5) says. Note that for elder and weak people just follow the Remo, כדאי הוא לסמוך עליו as soon as you think the rain won't stop.

  Source that a man is obligated first night: אמר רבי יוחנן משום רבי שמעון בן יהוצדק נאמר כאן חמשה עשר ונאמר חמשה עשר בחג המצות מה להלן לילה הראשון חובה מכאן ואילך רשות אף כאן לילה הראשון חובה מכאן ואילך רשות
  It says with regards to eating on Chag hasuccos (the festival of dwelling in the succa) Fifteenth and with regards to the festival of eating matzos fifteenth. just there the first night is an obligation as it says "in the night you shall eat matzos" so too the first night of the festival of dwelling in the succas, it is an obligation to eat in the succah.

• If you know the Succah will blow away as there is a hurricane building up, and its past shekia (sunset) and still not yet such strong wind that you can do kiddush and Hamotzi, then do Kiddush now and having a kzais in the Succah until its no longer safe (unless you have neighbors with indoor Succah that you can access safely even in the hurricane). This way you have at least done a Sofeik Mitzva deoraisa. The source that one should do a Mitzva deOraisa even in safek after bein Hashmoshos if not possible otherwise is the Ran (quoted Beis Yosef OC 665):

  ליכא למימר דמגו דאתקצאי לבה"ש אתקצאי לכולי יומא משום דלבין השמשות גופיה לא אתקצאי שהרי בין השמשות אינו ראוי למצות אתרוג שאפילו לא נטל כל היום אינו נוטלו בין השמשות דכיון דלולב בזמן הזה מדרבנן בר מיום ראשון ובין השמשות ספק הוא ספיקא דרבנן לקולא -
  We do not say since that an estrog was muksa bein hashmoshos on the 7th day of Succos which would make it subsequently mukza for the 8th day, because a person cannot fulfill his mitzva of estrog bein hashmoshos since anyway the 7th day is only chayav miderabanan and Bein hashmoshos is safek 8th day and safek derabbanan Lekula. Succah which is min haTorah all 7 days so one should eat even during Bein hashmoshos on the first evening after shekia*(without a brocho) when in doubt (of pikuach nefesh later on because a hurricane might blow the Succah away.)

---

*Source that after shekia (sunset) is safek Layla Min Hatorah as it says in Biur Halacha S.A O.C 261,2

ולשיטת הגר"א הנ"ל מיד אחר שקיעת גוף השמש מעל הארץ הוא בה"ש גמור וכנ"ל. ובאמת שיטתו זאת לאו חדשה היא דכבר הסכים כן בתשובת מהר"ם אלשקר סימן צ"ו דמיד אחר שקיעת גוף השמש הוי בה"ש גמור והביא שם שכן כתבו בפירוש הגאונים הראשונים בתשובותיהם והמה רבינו שרירא גאון ורב האי גאון ורבינו נסים גאון גם הרב ר' אברהם החסיד בנו של הרמב"ם ז"ל גם כתב שם שכן משמע מהרי"ף והרמב"ם ורש"י ע"ש והביאו הש"ך להלכה ביורה דעה סימן רס"ו סקי"א ).