Ok, first of all can I just assure everyone that I would NOT, repeat would NOT, do this (any of this) in real life. This (these?) is (are?) something I enjoy doing on the sims because I would never do something like this (these?) is real life. This challenge is just meant to be a bit of evil fun on the game, not something to repeat in real life.
A brief overview: Create a family and torture their lives with misery, cheating, death, divorce, rejection, illness and other smelly sims.
A more detailed explanation: Create an adult male in C-A-S. Move him into any sized lot you want (although I would recommend a small one) and build any house you want. Have him marry and have a kid together. Have that kid grow up and get married themselves. Have them and their spouse have a kid themselves. The aim is to keep this going for 10 generations. You only need one child (although more can be used) to carry on the family line and they must continue to live in the original house. Sounding a bit like the Legacy Challenge, isn't it? Well, it isn't ... read on...
THE TWIST: The idea of this challenge isn't to keep the family happy through 10 generations - the idea to make them miserable. Per generation, you have to inflict as many unhappy events on your sims as possible. I'm talking divorces, affairs, deaths, fired from job, children with an affair-ee (there probably is an actual name, but I don't know it,) illness, no money, needs low, aspiration failures, etc - you get the picture.
Point System: You start with 200 points per sim (the main family and spouses.) Play the sim through their life and when they are dying or in their last day of elderhood, look in their memories. Add 5 points for every bad memory (the ones with a red background) they have - they will all be miserable events; the kind of event this challenge aims to get. -5 points for each good memory (the ones with a green background) they have. If your sim experiences an accidental death and you don't get time to look at their memories, add 200 points - that is worth the amount of points you get for 40 bad memories, so about the amount you'd expect to get. The exceptions to the 'good memories point loss' are any unavoidable ones (eg: met whoever.) I don't really need to give a list, you're all sensible, you know what I mean. I'd just like to point out, however, that 'got engaged' and 'got married' are NOT included in the exceptions for user-created sims or kids in the main family line, because they are avoidable in these (the people the sims marry, provided they aren't user/maxis-created or part of a user/maxis-created family, are excluded from 'got engaged,' 'got married' and 'had a baby' because it's only one aspiration that sees them as bad and yuo are not in control of NPC or Townie aspirations.)
Rules: There are few rules, actually only one: No cheats - it's so much more fun to make sims miserable naturally. I like to make challenges as fun as possible, so that means not being restricted to all different things.
Enjoy torturing poor simmies with evil events, reply if you're taking part and please keep me updated on what you're sims are experiencing.