I would not recommend ever trying for baby, because oh my god can you even imagine, but if you have the Master Command Woohooer mod from SexySims, one thing that might spice things up is a risky woohoo pregnancy rate of 1%. Drama!!!!!
Leveling up charisma is SO USEFUL in this challenge. At level 7, my sim was able to seduce and woohoo with johns within one sim-hour of meeting them.
If you do this challenge let me know! I am amped as all heck to hear what others come up with!!
If you do end up beating the challenge, maybe consider having your main character have a kid to take over the family business one day!