This is mostly for my own use since I tend to change challenge rules a lot to fit my own playstyle--just sometimes I can't keep track of that shit.
I get bored of having money coming out my family's ears by the second generation in regular legacy challenges, so I...basically combined both the poverty and legacy challenge to see how well a family moves through the social classes through the years.
STEP ONE:
Make a single CAS adult. Randomize their personality/aspiration/turnons-turnoffs. Alternately, make a single CAS teen/adult combo and kill the adult off. Alternately alternately, make a single CAS young adult founder who you can take through college as long as they do not graduate with more than a C average. If you go the YA route, their skills/badges must be cleared once they become an adult so as to start on equal ground as a CAS adult.
STEP TWO:
Move your sim onto any lot, size does not matter. You're going to be tossing the extra money away anyhow.
STEP THREE:
Buy the cheapest shower and refrigerator. (If you do not have Uni and no access to the minifridge, you may also buy a single counter.) This is to remove the initial dependence on community lots, which is obnoxious to people who have slow machines/hate community lots.
STEP FOUR:
Reduce the family funds to zero. You can do this using whatever method you want. You may also use this money to add flavor to the lot via landscaping or what have you, as long as it does not benefit your sims in any way. The only caveat to this is whatever you buy with this money cannot be sold unless you immediately get rid of the money gained by selling.
General Rules/Restrictions
--You may only move in sims who will directly contribute to the next generation. (Marriage optional.) What you may not do is keep the money they bring. Gotta shred it or do more landscaping. Because of this, there are no restrictions on moving in Mr. Big/The Diva/Grand Vampires. If the sim happens to move in with items in their inventory, those items cannot be used or sold unless it's a ReNuYu Porta-chug.
--You may adopt as long as you have money to do so, but the heir each generation must be able to trace their bloodline back to the founder, so adopted children are ineligible.
--Every generation, roll a single 6-sided die. Whatever you get will be the number of children the heir must have before becoming an elder. Adoptions and children taken by the social worker will still count towards this total unless the number rolled was one. (There must be an heir.) None of the children need to have the same parents.
--All elders must quit their jobs on their birthday; they may not retire. You may keep them around for as long as you wish to take care of children, or you can move them out. They simply may not make any money.
--Once the youngest child of a generation ages to adult (or goes to college), all sims except the heir, spouse of the heir, and children of the heir must be moved out.
--You may own pets, but you may not sell them to passers-by. If you want to get rid of a pet, you must put it up for adoption.
--You may not make money in any capacity outside of careers. This includes, but is not limited to:
No selling paintings
No selling novels
No selling items from crafting benches
No selling restored cars
No working as a DJ/bartender
No selling financial advice
No home businesses
No competitions
No selling fish/produce
No pool hustling
No buskering
No career reward objects that generate revenue
No selling pets
Etc...
Basically, if you can make money with it and it isn't a job you get in the newspaper/computer, assume you are not to do it. All money gained in this way must be destroyed. However, you MAY keep the money that you make entirely by chance (school chance cards, job chance cards, etc).
Note that you may still paint paintings, write novels, craft items at benches, restore cars, etc, you simply cannot sell what you've made. You can drop them into sim inventories or sell it in buy mode and destroy the money gained.
--You may use service sims as long as you can afford them.
--You may use any aspiration or career reward as long as they don't make money. Exceptions: no Elixir of Life or Cow Plant.
--You may sell any item you've bought with your own money at any point.
--You may sell gifts given to you on dates, but only after they have depreciated to their minimum value. This is to reflect basically pawning the stuff off. If you don't want to sell them, they are free to be used.
--You may not take advantage of player-owned businesses where everything is set to the cheapest price. You may use player-owned businesses where the objects are sold at "expensive" or higher.
--You may not skip chance cards. Ever. Even if it's really unfair.
--Promotions via chance cards are legitimate and you may retain the position even if it puts you over the max job level of that generation. Money gained from the promotion bonus may be kept.
--If you get fired from a career (either by poor job performance or unlucky chance card), your sim cannot take another job in that career again unless the Free Time "plead for job" option succeeds. After being fired, you must wait three days before taking another job.
--If you get an accidental (non-chance-card) promotion that puts your sim above the max allowed job level for their generation, you must quit the job immediately and shred the promotion bonus. You may immediately take another job and it can be in the same field; however, any promotion bonuses for career levels below where you quit must be shredded. (Say Sim A from gen 5 accidentally gets a non-chance card promotion to level 6 in Medicine. Sim quits, bonus gets shredded, and he immediately retakes an entry-level Medicine job. All promotion bonuses up to level 5 must be destroyed.)
--Once you're on a career path, you must keep that job. Quitting is allowed, but once you do so, you cannot take another job for two full sim weeks. If your sim becomes an elder in the interim, you cannot retake another job at all. This is to prevent promotion bonus abuse.
Generational Restrictions
Generation 1:
--Founder and spouse may only work entry-level jobs.
Generation 2:
--Heir and spouse may only work 2nd level jobs.
--May go to school as a child, but may not go to school as a teenager.
--No private school.
--May not go to college.
Generation 3:
--Heir and spouse may only work 3rd level jobs.
--May go to school as a child and teenager.
--Teenager may not get a job.
--No private school.
--May not go to college.
Generation 4:
--Heir and spouse may only work 4th level jobs.
--May go to school as a child and teenager.
--Teenager may get a job.
--May not go to private school.
--May go to college if they receive $3000 or more in scholarships.
Generation 5:
--Heir and spouse may only work 5th level jobs.
--May go to school as child and teenager.
--Teenager may get a job.
--May go to private school only if the gen 4 heir went to college.
--May go to college if they receive $2500 or more in scholarships.
Generation 6:
--Heir and spouse may only work 6th level jobs.
--May go to school.
--May get a job.
--May go to private school.
--May go to college if they receive $1000 or more in scholarships.
Generation 7:
--Heir and spouse may only work 7th level jobs.
--May go to school.
--May get a job.
--May go to private school.
--May go to college.
Generation 8:
--Heir and spouse may only work 8th level jobs.
--All Gen 7 rules apply.
Generation 9:
--Heir and spouse may only work 9th level jobs.
--All Gen 7 rules apply.
Generation 10:
--Heir and spouse may reach the top of their career.
--All Gen 7 rules apply.
Rules on Inheritance
--You may not accept inheritances from friends who have died. That money must be destroyed.
--When it comes to inheriting the money of dead parents, you must
randomly generate a number between 1 and 100. This is the chance your sims will be able to keep the inherited money.
Generation 1: N/A.
Generation 2: 1-90, the money must be destroyed. 91-100, the money may be kept.
Generation 3: 1-80; 81-100
Generation 4: 1-70; 71-100
Generation 5: 1-60; 61-100
Generation 6: 1-50; 51-100
Generation 7: 1-40; 41-100
Generation 8: 1-30; 31-100
Generation 9: 1-20; 21-100
Generation 10: 1-10; 11-100
The reasoning behind this is that the more the family progresses in job levels, the more chance a sim will leave behind money when they die.