This is intended to be a difficult, but not impossible, challenge, comparable to the first generation of an Apocalypse. Just like real-life homelessness is difficult but not impossible, your sims will have a hard time of it, but--barring horrible luck or deadly mistakes--they can come out of it safely... if you're good enough at managing them.
This challenge requires two mods:
• You need to install the Homeless career. This works just like any other custom career--stick the file in your Downloads folder and you're done. (To uninstall, remove the file.) ** LINK TO THE HOMELESS CAREER: http://simfileshare.net/filedetails/178983/
• You need to have a way to cheat sims into the career. I recommend the Sim Blender. (Installation is the same as any other CC; just download and stick the object into your Downloads folder. The Sim Blender itself can be found in the Miscellaneous section of the Miscellaneous tab; it looks like a potted plant.)
Create a single adult sim in CAS (or equivalent). If you want an easier challenge, you may put him through college first, but he must come back with nothing in his inventory and no money beyond what the game gives Uni graduates. Aspirations are random, though you may choose secondary aspirations if you have FreeTime. You choose everything else about the sim.
You may choose your neighborhood's seasons as you desire, but there must be at least 1 Winter and 1 Summer.
Move your sim into an empty 5x5 (large) lot, as you would if you were starting a legacy, and cheat him into the Homeless career. I recommend the Sim Blender for this purpose. (You could just wait for the career to show up in the paper, but this can take a week or more and your sim won't survive that long. If your sim is fired, you may cheat them into the career again.) This career is extremely demanding and earns very little money, and is designed more as an impediment than as a benefit. Beware!: How you spend your starting cash is very important. Your sim will start out at a salary of $10 per day, and it doesn't get much better. To aid you in planning, the Homeless career depends on Body, Charisma, and Creativity skill.
If you are posting a story out of your challenge, you may prepare your sim's lot by adding any Build mode items which sims cannot actively use (ex., you can place a wall or a tree, but not a fireplace or a pond). The sim must have the same starting money as if he were moving into an empty 5x5 lot, and you may not have any enclosed rooms or a roof/ceiling of any sort. (Go ahead and use the familyfunds cheat to get the money right.) The Environment boost is your reward for writing the story.
The goal of the challenge is to break the cycle of poverty by sending a teen sim to Uni.
• No sim on the lot may ever hold a career that is not in the Homeless career track. No teen on the lot may ever hold a job at all.
• You may not use any cheats or CC items that give you an advantage. Purely cosmetic cheats/CC, macros, annoyance-savers, bugfixes etc., are fine.
• You may, at any time, cheat to enter an Adult living on the lot into the Homeless career.
• All primary aspirations are to be rolled randomly.
• You may move in only Townies and service sims. If you move anyone out, they may not move back in.
• The lot on which your sims live may not have any enclosed rooms or any roofs. (Fences are OK.)
• When an adult sim moves into or grows up on the lot, you must cheat him into the Homeless career. No one may quit the Homeless career, and you may not cancel "Go to Work" from a sim's queue, but Elders may still retire. Fired sims may remain unemployed or you may cheat to enter them into the Homeless career track.
• You may never ignore chance cards.
• Being without proper food preservation, your sims may never store food in their inventory or store leftovers in a refrigerator.
• Birth control is not available. "Try for Baby" must always be chosen if it is an option.
• Your sims' basic needs are their first priority. You must select all four Needs aspiration perks before selecting any other perks.
• No sim living on the lot may visit a community lot (any lot other than the home lot) more than once in any given week. After twelve hours on a community lot, the cops run your homeless sim(s) off, and your sim(s) must return home. (Your sim can leave the lot early and spend the remainder of the twelve hours on another lot, if desired, but must spend no more than twelve hours per week on community lots.)
• Your sims may never Plead with the Social Worker or with the Grim Reaper. The world simply doesn't give them a second chance. (If you have Witches, it is still permissible to resurrect or zombify deceased sims.)
• You may not have more than a certain number of items of the following types placed on the lot at any time: Buy mode items, aspiration rewards, career rewards, the Pool tab, and completed crafted items (from a workbench, easel, cauldron, etc.). All other items must be sold or in inventory at all times. Whatever cheat object you use to cheat sims into the Homeless career track doesn't count toward this limit. Bugfix, posebox, macro, or similar CC objects also don't count. (Yes, that means you're allowed to use cheats to change your sims' appearance to a more realistically scruffy look... though it may be to their advantage not to look homeless, of course!)
• The limit on items placed rises with the number of sims on the lot. With one sim on the lot, you may have three items. Each additional sim living on the lot allows one additional item, to a maximum of ten items with a full lot of eight sims.
• All other items do not count for this limit; for example, there is no limit on things like plates of food, newspapers, books from the bookcase, and Build mode items other than the Pool tab.
• If your sims are given items which exceed the limit, immediately put them into inventory.
• Every night at midnight, you may return items to your sim's inventory or sell them in Buy mode, opening slots to place other items during the next day (up to the limit).
• Humble's computer must be deleted unopened.
• Anything your sims buy from a sim-owned store must be priced at least "Cheap".
• To move someone onto the lot in any way other than being born on the lot, they must have a 100/100 relationship and be in Love with someone living on the lot. (Yes, this means no adoptions or Servos.)
• Your sims may eat fish they catch and crops they grow, but may not sell them.
• Your sims may create and use workbench, easel, cauldron, and other crafted items, but may not sell them.
• Your sims may not own a business or a vacation home.
• Your sims may not go on vacation.
• Your sims may not dig for treasure.
• You may have no more than one Snapdragon on the lot at any time.
• No sim living on the lot may go on more than one date or outing in any given week. Weeks start on Sunday at midnight.
• Witch Thrones may be used only by the witch that created them. (That includes the Thrones at the Evil/Good witches' castles; since your sim is not a Head Witch, they may not use them.)
Breaking the Cycle:
For your homeless family to send a Teen sim to college, the following requirements must be met:
• The Teen sim must have been born on the lot.
• The Teen sim must have at least ten scholarships. (For reference, scholarships include: Seven scholarships, one for each skill of 8 or higher; Scholar's grant for A- or better grades; Extraterrestrial Reparation for alien abduction, Undead Educational for zombie or vampire, Billiards Prize for high pool skill, Footwork Award for dancing skill, and Orphaned Sims Assistance Fund for sims with no living parents. The Young Entrepreneurs award is impossible because teen sims cannot get jobs in this challenge.) For a harder challenge, the teen sim must have at least twelve scholarships.
• Both of the Teen's parents must be at level 10 in the Homeless career, or have retired from level 10 of the Homeless career.
• Items should be as useful as possible. A tent or double bed allows multiple sims to sleep and allows WooHoo; a single bed only sleeps one.
• Sims who are in a bad mood won't automatically go to work--useful if you want to get someone fired so they can stay home with a baby.
• Your sims will be constantly exposed to the elements. Remember that fireplaces are Build mode items and don't count toward the item limit, and that babies can be timed so that they will grow up during seasonable weather. Also, Making Out raises Sims' temperature.
• Items used from inventory don't count toward the limit. That includes things like cell phones and fish (and magic reagents, but of course the cauldron where you create them counts as a placed item.)
• Playing music or freestyling for tips is still allowed, but will only be profitable if you can gather the required musical instrument, creativity points, free time, and visitors to tip. "