The challenge sounds interesting. I also prefer challenges which are a bit less frustrating. I never do challenges with scoring or time pressure.
I think the way you will raise the kids is very similar to what I have in mind to start your previous challenge. My sim who will complete all aspirations will start born in game and complete all toddler skills and childhood aspirations before growing up. Are you also going for the character values from parenthood (if you have that pack) ? I plan to do that, but only for one sim. ;)
I don't know if I could do all of this 100 times though. I am curious to see how it goes for you.
The twins are a nice surprise. :grin: