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According to my minhag: on the first night of Sukkos by Kiddush, Leishev Basukkah [לישב בסכה] is said before the bracha of Shehechiyanu [שהחינו]. On the second night, however, Shehechiyanu is said before Leishev Basukkah.
According to other minhagim: Leishev Basukkah is always said first.
So what's up with that? Why should one be said before the other? Which should normally be said first? And why the switch for me?
The proper order of these blessings is a machloket between Rav and Rabba bar bar Chana on Sukkah 56a. Rav held the blessing on the Sukkah comes first because it's the obligation of the day and Rabba bar bar Chana held that Shehechiyanu comes first because it is Tadir = said more often. The Rambam (Sukkah 6:2) rules like Rav and Shulchan Aruch does likewise in OC 643:1.
The Tur (OC 661) quotes two opinions regarding the second day. The Rosh holds that the order should be flipped and the Avi Ezri holds that the order should remain the same. At first glance the Avi Ezri makes the most sense: when else do we distinguish between the different days of Yom Tov? We say a Shehechiyanu on the day in case it is really the first day, shouldn't we say a Shehechiyanu on the Sukkah in case it is really our first time performing the mitzva?
The answer lies in the nature of the Shehechiyanu on the Sukkah. It is not being said on the new mitzva performance, but rather is said upon building the sukkah and can even be said many days before the holiday starts (OC 641, note also our custom to use the Shehechiyanu on the holiday to fulfill this obligation). Thus even if the second day really is the right day, we have already fulfilled the obligation of Shehechiyanu on the Sukkah the previous night. (This is also why we don't say a Shehechiyanu on the Lulav on the second day of Sukkot, but we do on the Shofar on the second day of Rosh HaShana.)
(I'll note that neither Rav nor Rabba bar bar Chana seemed to care that the Shehechiyanu be after the Sukkah in order to have the Shehechiyanu apply to the Sukkah as well, ie Shehechiyanu should apply to everything by default anyway. Tzarich iyun on the Rosh IMO.)
The Shulchan Aruch and Rama rule like the Rosh, while Bach, Maharshal and Gra rule like the Avi Ezri (see more names on both sides in Shaar HaTziyun OC 661 sk 3) and hence the differences in custom.
First night: say a leisheiv. Then say a shehechiyanu, as that is covering both the yomtov (shehechiyanu is part of the standard kiddush of the first 2 days of pesach and shavuos too), and the new experience of the mitzva of dwelling in the sukkah (just as you'd make a shehechiyanu the first time you take a lulav, but not subsequent times).
Second night: well as a rule of thumb on yomtov, the Sages enacted a shehechiyanu for the second-night-yomtov kiddush, to generate more respect for the second (rabbinically-enacted) day. However, it's not your first time saying a leisheiv. Therefore:
Custom A: Make regular kiddush, including the standard second-day shehechiyanu. THEN, make a leisheiv, which will be immediately followed by your sitting down and drinking in the sukkah (so your "dwelling in the sukkah" came immediately after the blessing to do so).
Custom B: We don't want people to treat the second day as any less special than the first day. The rest of the prayers are the same for both days. Therefore, say the exact same kiddush as day #1, i.e. concluding with shehechiyanu.
I can answer your family Minhag based on the following logic:
The Shehehiyanu is on the Mitzvah. In the case of the first night, two Mitzvoth are being performed for the first time. In the second, the Mitzvah of "dwelling" in the Sukkah has already been performed. However, the Yom Tov and Kiddush obligate a Shehehiyanu.
Why you would say Shehehiyanu on Kiddush of a second night of Yom Tov is an interesting question all year round.
I remember hearing what I thought then was an interesting approach, which explained why others don't follow this pattern, but I don't remember what that was, unfortunately, and I was thinking about it this year wondering if I should follow that or what my Mahzor said (it was the first year it was applicable to me making Kiddush on the first night of Sukkoth). I should have looked this up before Yom Tov. :(
