Rags to riches challenges are pretty common in the Sims. Today, we are going to do the exact opposite! Start off a sim as fabulously wealthy and UTTERLY RUIN THEM!

Preparation:

1. Create a single sim, Any age, gender, supernatural status or trait combination you'd like. (Maybe even base them off of a real-life Billionaire or Celebretiy you happen to loathe!)
2. Move them into the world of your choosing, and Use cheats to earn them at least 1,000,000 simoleans. Give them a sweet mansion to live in.
3. Become friends with all the other wealthy sims in town (Anyone whose family has at least 100,000 simoleans in spending cash) Upon earning the admiration of your wealthy peers, It's on to the next part of the challenge!

The Ruining:

1. Ensure That this sim is never actually employed. They are a Trust Fund Baby who thinks they can do whatever they want, and that the money will never run out, so there is no need to get a job. Also, Never pay any bills, so that the money does actually bleed away.
1a. Eventually, the Repo-man will start to come around to collect items for non-payment of debts. Replace these items as long as you are still able to afford them.
2. All those wealthy sims you befriended in the first part of the challenge? Become enemies with them all! Doesn't matter what you do to earn their scorn, just ensure that the former friends become current enemies.
3. Any Lifetime reward that earns you money or the "No Bills Ever" reward is expressly forbidden.
4. You are also forbidden from buying real estate around town.

How do you know when the challenge is over? Well...

Rock Bottom: Conditions for victory

1. The Sim's Bank Account has reached zero simoleans.
2. Every single person in town hates them.
3. The Repo-man has taken so many items from their property, that you can no longer afford to replace necessities (Fridge, Toilet, Bed, etc) and the Sim is forced to go off-lot to replenish these needs. That mansion is now an empty husk of its former grandeur.

Have fun!