I have been playing the challenge for two and a half months now. So far these have been my experiences:
1) To get a lot more money and buy better essential home objects that would not cause the uncomfortable moodlet, I tried moving in either the Landgraabs or the Calientes.
2) Since I moved in a lot of people, I had to wait a while before producing children. I usually start at adult.
3) I observed some of my teens can't get past the current grade even if I've done all the requirements (competed homework, extra credit and go to school focused).
4) I missed the part on the instructions regarding the BFFs: One heir's BFF must not be the BFF or Good Friend of another heir.
5) Having someone in the household with Handiness, Mixology, and Cooking/Gourmet Cooking skills at high levels can give a lot of Happy boosters to the required emotion. Upgrades such as clean coat for bathtubs, pulsating jets for the really nice bathtubs, shower upgrades, auto soap dispenser for faucets etc. sometimes give Happy boosters. Mixology drinks such as Prose and Pop, Sunset Valley, and Sour Punch give strong Happy emotions, sometimes even +4 if your sim is a Foodie. Baked Alaska (Gourmet Cooking level 10) can give +4 mood if your sim is a Foodie.
Really bummed about the BFF mistake. Oh well.