Hi!
So I've been giving the Legacy challenge a try. So far it's going REALLY well. Almost too well - it's easy?! So, I (think) I am following all the rules. I am on generation 2 - my founder's daughter is a YA - and married, but hasn't had any babies yet. Money hasn't been a problem for a long time, and both the founder and her husband have around 150K Lifetime Happiness points. I've been able to purchase all sorts of goodies with the points! They have also both fulfilled their lifetime Wishes (Perfect Garden and Professional Author) while also reaching the top of their career tracks.
It looks like from here on life will be easy for my sim legacy. I wonder if others are finding it this easy? I admit living on an empty plot with only a bed and a toilet for a little while was rough, but we got over that quickly :)