By Rabbi Simcha Werner
You should have enough Tea Lights/Candle holders for both nights, since it is questionable if you may clean out the wax on the second day of Yom Tov when you light candles. It is forbidden to melt the wax of a candle on Yom Tov to make it stick. When lighting candles on the second day of Yom Tov, make sure that the fire comes from an existing flame.
Regarding the Lulov and Esrog
The Daled Minim must belong to you the first two days. The same Halachos which are in regard to children before Bar and Bas Mitzvah the first day, pertain to them the second day. Therefore, just like you cannot give them to your child on the first day, unless you hold the Lulov and Esrog with him, so it does not become his, the same pertains on the second day. When all the adults are through benching Lulov and Esrog the second day, then you may give it to your child.
There are three Mitzvos of the Torah, Tefillin, Tzitzis and Sukkah which has a Torah obligation to have in mind the reason of the Mitzvah. One who doesn’t, even though he fulfils the Mitzvah, it is not being done properly. It's missing the effect that the Mitzvah has to have on him. “A person has to have in mind when he sits in the Sukkah, that he is sitting there in order to fulfil the Mitzvah of Hashem, that He commanded us to sit in a Sukkah, a remembrance that he took us out of Mitzrayim.” This is a free translation of the Alter Rebbe’s words. This Kavanah is a must. Before eating something in the Sukkah, especially the Challah on the first and second night, we should have in mind that Hashem commands us to make a Sukkah in order to remember the Clouds of Glory (Ananey Hakavod) that surrounded us when He took us out of Egypt so that we remember His wonders and awesome actions.
Wine on Yomtov
During the meal on Yom Tov men over Bar Mitzvah should drink a Revi’is of wine for Simchas Yom Tov. On Chol Hamoed, during the day one must drink a Revi’is of wine.
Children in The Sukkah
Boys who are not dependent on their mothers should eat in the Sukkah. This is usually from age six or if he is smart and mature, it could be even younger.
A common activity for Chol Hamoed is fruit picking. One may only collect that being used for Chol Hamoed or Yom Tov.