Halfway through this challenge I had an idea: as a continuation, in the end, when your family hits $0, you must move 1 or 2 sims to an empty lot (use money cheat to pay for funds for this lot, then set back to $0), and try to survive and regain your money. I recommend choosing a painter/musician to make money early on. The rule is that you can't get a job until you have $500, a bed per sim you have (if it's a couple you may have a double bed), a fridge for quick meals, a toilet, and a shower on the empty lot.