Here's a collage of this year's succah decorations. We've had our own family succah all but two years we've been married, though neither my husband nor I grew up with a succah.
I remember that our Oakland Jewish Center, Bayside, NY, Hebrew School had us "decorate" or enter a succah before the holiday. There was a major "disconnect" concerning Succot, because it wasn't a holiday we really celebrated. School in our very Jewish neighborhood was cancelled on Rosh Hashanah and Yom Kippur, but not Succot. I do have some memories of visiting the Rabbi's home and seeing a decorated hut by their house, since my aunt was a close personal friend of Rabbi and Mrs. Issacson. But until I began becoming religious in high school, after we had moved to Great Neck, Succot Holiday and the sukkot huts weren't part of my Jewish Life.
My husband's family was more traditional, but they lived in an apartment, so the succah was just whatever the shul had built.
Our first year married and in Israel, we lived in the Maon Betar in Jerusalem's Old City. We didn't have a succah, but we carried our main meal to the Bnai Akiva succah, which wasn't all that far away. The following year, we were in our very own apartment in Bayit Vegan, which actually had two balconies suitable for a kosher succah.
The first years we used the one off of our bedroom. A close friend met my husband in Machane Yehuda and helped him buy all the equipment needed. Then she came over to help assemble it. We didn't even have enough chairs for all the guests we had invited. I don't know how we fit everyone into the succah for the meals, but we did.
When we planned our Shiloh home, a 2x5 merpeset seemed nice and big, but now, bli eyin haraa, we can't fit the entire family inside the succah, unless we just stand sans table. Or we can have a small table as buffet and stand around it eating. The kids decided that they're coming over for lunch before Simchat Torah, a time when we can eat indoors.
Now I'm looking forward to the holiday and wonder when the rains will start.