Plot:
You fell victim to a fraudulent partner, leaving you in dire financial straits. As debts piled up, you were forced to sell your home, prized possessions and family business.
Your goal is to build a new home, start a family and a private business. In each generation your home have to get upgraded, have extra offspring, and better and wealthier family business.

Rules:

1. Create a Sim and pick their gender. Their personality and favorites have to be randomize. Fortune / Living in the Lap of Luxury should be their lifetime wish.

2. You move to a 4x4 or 5x4 lot. Own a tent, bonfire, small end table and a stereo. Your funds are 10 Simoleons.

3. The jobs you are allowed to be accepted for are the jobs that don't require a degree, such as Criminal, Culinary, Slacker, Gamer, Artist, Bookstore Clerk, Grocery Store Clerk, Mausoleum Clerk, Receptionist, Angler, Gardener, Photographer, Writer, Sculptor, Band. To get a better job you have to go to university.

4. Your partner and future partners of offspring, and offspring as well have to follow rule number 3. The only way to get a better job is by going to university.

5. You can take care of your needs in public areas. Build your house layout and buy new home necessities.

6. You are allowed to build a relationship but can not move them in until you have basic looking house, necessities and furniture.
Once you have a home and a partner, your goal is to have 1 baby. And open a family business.

7. In each generation the offspring should have at least 1 to 3 children. The house and the family business are going to be inherited by the eldest child. And they take responsibility in upgrading the house and the business when they age up to teen. You have to use a dice to decide for you how many babies the next generation will have (1-3 babies).

8. No family member leaves the house in all generations, you must plan what everyone will do for the benefit of the house and the family business. And continue to bring offspring for future generations until you have your dream home and successful business.

9. Have household net worth of 100,000 Simoleons and 100,000 in cash to win the challenge.


Happy simming

One small note here (based on my husband who works in a professional kitchen). Culinary careers often do require you to have a culinary degree, especially at high end restaurants. Like the diner you could progress up just on talent and experience but at the bistro you'd likely be capped at level 3 or 4 (depending on what the executive chef is looking for in an employee). You could probably push level 5 or 6 but you would have to have a lot of experience. In the Sims, the degree for culinary is fine arts.

You could probably also put music on the list but specify the rock star branch only. There are some music stars that have gone to arts school but it's probably only required for the classical music branch.

It definitely sounds like a challenge though, especially getting a house big enough to fit everyone

Thank you for the suggestions, that sounds interesting. I wasn't sure about Culinary, but in the Sims they always start as a dishwasher. It also takes into account another mod career, for example a waiter.
About a music career, probably a band or solo can work. I will add that as well =)
I hope you enjoy the challenge!

After real life got out of my way, I started. I did make some personal rules. First, because I play on long lifespan, I'm doubling my goal of net worth and cash on hand. I'm going to not do adventures even when I get the cash because one trip to Egypt can net you a pocket of cut gems just by clearing the Spinx tomb lot- which allows you to start making a profit on a 3 day trip immediately. Likewise no turning into a supernatural and no using alchemy. I'm going to use the well mod plus candles for lighting until I can afford to buy a decorative or functional solar panel. I'm also starting in winter to keep me from getting too much free food out of the public gardens.

Button smashing got me Monica Andrews: schmoozer, bookworm, loser, light sleeper (that's going to be fun sleeping in a tent), technophobe (interestingly enough the Scribbling Pad, updated here , was the first thing I downloaded from here). I will admit I hit random until I got a set of traits that were base game only since most of the expansion ones tend to be mostly positive and/or only useful to that expansion. She likes stew, electronica, and the color "spice berry". With the bookworm trait, I'll be aiming for a family business of making a family run publishing company (with everyone being eventually just self supported writers).

I picked Twinbrook as my starting area and gave her the swamp lot behind the spillway. On her lot I also tossed some reeds and some 0 cost junk items (like the broken truck from Supernatural) and went ahead and gave her a low cost chair for her fire pit since you get free chairs with it anyway. After deleting the free $800 camera in her inventory and the free university welcome kit, I got started.

Day 1, I immediately got her a job at the bookstore then hit the Twinbrook gardens lot. After getting some food she had a negative moodlet from getting cold and her hygiene was at 0. She warmed up in the bathroom and ate an apple then headed to the park. She found a few flowers at the park (I have a mod that halves how much wildflowers sell for) but immediately got hit with the negative, 2 day moodlet allergies and definitely does not have the $200 to get an allergy shot. I figured at this point, I might as well have her go dumpster diving since she had 0 hygiene anyway and for some reason sims have fun while doing it. While she found a few good things to sell (and a soccer ball to keep for when sheen needs some fun and has energy to spare) she also picked up the negative moodlet nauseous. At that point it was getting very late so I had her hit the gym to shower and wait for her to throw up when nauseous wore off. She crawled into her tent at about 1 in the morning having scrounged up food to roast at her fire pit in the morning and a couple hundred dollars to help cover the first few bills.

Hopefully before work on day 2 she can get a few skills. I need to buy her a scribbling pad and an umbrella (I have Tempest which means while it doesn't get cold in the winter, the predominate weather in Twinbrook is rain). From there it will be buying a well and some jugs before hopefully getting at least a toilet and sink. For anyone else who plays this, that $10 will not be enough for your first round of bills so you will need to immediately get at least a little money.

Thank you for sharing your game, I hope you enjoy the challenge so far!