I've combined the Rags to riches challenge and the 100 baby challenge together and here are the rules. The challenge has been fun for me so I thought I would add the rules I've made for it here in case anyone else wants to join in! Please note that this challenge is written with a female sim in mind, if anyone wants me to I will try to write a different set of rules for the men sims out there.
Rules for rags to riches 100 baby challenge
1) Have to start off on an empty lot with 0 money. (Like a normal rags to riches)
2) Has to have a house before getting a job, (Bedroom, bathroom, kitchen, living room. (Like a normal rags to riches)
3) Has to have a house before having a baby
4) Your sim has to be pregnant with another baby before aging the already existing baby up.
5) Toddler has to learn all their toddler skills to the max before being aged up.
6) A child has to earn all their childhood skills to the max and have an A+ in school before being aged up. (If you want you can make it so they have to get to the highest part of the Drama or Scouts club before needing to age up)
7) Teens have to get at least one skill to the max, get an A+ in school, and get to the top of a part-time job before aging up. (Might add more later)
8) When the teens age up into young adults make sure they get a job and then move them out of the house, you can make houses for them or use preexisting houses.