REQUIRED EP's/SP's: University
Intro, details, and objectives.
You didn't choose to be homeless. Every day you try applying for jobs but are rejected because the employers think you'll scare their employees and customers away. Why did this happen? Because a drunk man by the nickname of 'Not-So-Pleasant' happened to be drunk driving. When he hit you, your face became deformed. Ever since then you've been seen as a monster, and people often treat you like you're handicapped or had a major birth defect. Can you manage to get a good, well-paying job and have children?
Another objective of the challenge is to be able to have "enough simoleans" to "purchase" a surgery table. (I know, it's a career reward, but pretend it's not, m'kay? And the first time we use it to make the appearance of the Sim ugly, does not count because it IS NEEDED.) The "price" of this surgery table is $1,000, but your Sim can only afford it if they have a child and that child grows up normally. This child helps pay for the surgery table so your Sim can get a job. The child MUST become an adult and if you want, can skip college. College is a waste in this challenge.
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Okay, before moving on to the rules, you must know how you should make your Sim:
-Do NOT make your Sim deformed YET; we need average, decent, or pretty DNA!
-Other than that, make your Sim look any way you want. Just not really ugly or deformed.
-Once your Sim has been made, put them on the lot (details below) and type in the cheat code "unlockcareerrewards". Select the surgery table and make them ugly... unless the surgery table beats you to it!
The Lot
-The lot must either be empty, look like an alleyway (for hobos), or be a shack with one room.
-Fences/dividers are permitted.
-Lot must not be worth over $5k.
-Have the necessities, as you are not allowed to delete or sell any objects.
RULES
-Your Sim may NOT have a job of any kind.
-Your Sim is permitted ONLY $12,000, and you may not receive any money. This is kind of a life savings that your Sim had before the accident.
-You may NOT delete/sell objects of any kind, including furniture, pottery/other works of art, flowers, necessities, walls, etc.
-Aging MUST be turned ON. You may not turn it off any ANY point of the challenge.
-No cheats at all!
-Your Sim cannot have a fancy or decent house; if they don't have a job, how can they pay for it? (See "The Lot" above.)
-Your Sim may NOT have any electronics of any kind, including phones... okay, okay, one exception: Robots! They may have robots, bought or crafted.
-You may not use hacks or mods that may go against this challenge. Only object RECOLORS are allowed; hacked objects like casino slot machines that give you money are NOT permitted.
-No one may move in until your Sim becomes an elder. If they move in, they CANNOT be rich, including The Diva or Mr. Big.
-When the offspring grows up into an adult Sim, they MUST get a job in order to "pay" for the surgery table.
-When the offspring grows up into an adult Sim, they are allowed to move out.
-When the offspring grows up into an adult Sim and gets a job, they MUST make it to at LEAST level 5, no matter what career it is, custom or not.
NEW, ADDED 8/18: -When the offspring becomes a teenager, they may NOT have a job BUT they CAN make money from selling crafted items.
Scoring
Good:
+100 if your Sim's child grows up as an adult and "pays" for the surgery table. (Children are optional. Besides this, there are no benefits.)
+50 if your Sim reaches the top of their career WITHOUT CHEATS *after* they get the surgery table from their grown child and use it. If there is no child, your Sim may not have a job. It must be an adult Sim that is the child of your sim that can "afford" it. (Price of surgery table above, in the objectives section.)
+5 for every new friend your Sim makes
+10 for every new best friend your Sim makes (so you'd end up with 15 points total from making that best friend)
Bad:
-15 for every aspiration failure.
-30 for every enemy made.
-50 for every cheat used. If your Sim dies, sorry! You can't use maxMotives or boolProp. A death is a death, you can't literally cheat death. You fail the challenge if your Sim dies, ends up with $15 or less, or has a child but dies before the child buys them the surgery table. (Once a child turns into an adult, they can buy the surgery table whenever wanted. Price in objectives section above.)
-5 for every object destroyed by an animal, including dogs and cats.
-5 everytime something breaks, but you get your 5 points back if your Sim fixes the item within three Sim days.
-20 for every fire/burglary.
-20 for every person that moves in.
-40 if the offspring is/are taken away by the social worker.
-40 if the offspring die off before becoming full adults. (Young adults are NOT adults!)
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If your Sim has a child, anyone can be the father, as long as they don't move in or marry. (Exception if your Sim is an elder; then that person may move in, but they may NOT have more than $15,000 in funds; see Rules.)
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You Fail the Challenge If:
-Your Sim dies before their offspring buys the surgery table
-Your offspring dies before being able to buy the surgery table AND your Sim is an elder
-Your offspring loses their job before paying for the surgery table/getting to at least the fifth level
Questions? Suggestions? Please comment below!

Um,Actually,i dont think the surgery table does that.I think your thinking of the chair in OFB that does that.

No. What I meant is, you make the Sim like normal. Then after you move them into a lot, you use 'unlockcareerrewards' to get the surgery table. Then you use it to deform the Sim's face. The OfB chair only changes the make-up, accessories, and hair.

Some notes:
- Although there's no 'no community zone' rule, without phone, you cannot go anywhere unless you have Bon Voyage. And you cannot buy grocery, unless you have Seasons to grow/catch food(However, there're modded objects for farming without Seasons)
- You may need to grow up your child as fast as possible(with birthday cake when notified), including sending your teen to college(if you have University), if you want to get the job and reaches the top(with adult career).

LFact: You don't need Bon Voyage to walk to community lots. I don't have Bon Voyage, but my Sims can walk to different places. I think that the EPs after Bon Voyage also enable the feature: Freetime and Apartment Life.

Lavaster: So--the idea is that your Sim remains homeless until their kid grows up and gets a job, and then they can go back to living normally? If so, how can the Sim pay the bills? Is S12000 enough to support them until the kid grows up?

If you have very cheap furnitures, it may possible. One of my sim lives at junkyard(which is filled with decorative 'junks') pays hundred or something for bill. Except decorations, she has a tent, a mini fridge, a cheap plastic chair, and custom outhouse and shower.

I may end up increasing the money allotted.
And yes, the idea is for the kid to grow up and get a job. They must be an adult because the Center of Cosmetology for Adults refuses to sell any of their services/items to teens/younger.
A job IS required to purchase the table.
8/15/2010 10:34 PM UPDATE: I have updated/revised the rules.

I think it was Open For Business that started the feature. When I had just Nightlife and Universty I didn't have the option, but once I got Open For Business I did.

Well, when I got FreeTime I got the option. Maybe a patch added it?

Probably.

I see. Since I installed all EPs I have, I don't know what EP adds what well(except roof slope slider...).

lol, we're all having this little friendly debate about which EP walking to lots came with!

I believe it was Bon Voyage. Check on the thread for the original Homeless challenge or look in the Wiki.

If you need a phone for transportation only, build a residential lot and then open the cheat box, type "changeLotZoning community" and exit to neighborhood (save). Then open your lot again, buy a pay phone, and enter the cheat "changeLotZoning residential" ... You will now have a phone that can only be used for taxis.

@Katalina: There was another Homeless thread? I had a feeling mine wasn't unique.

Gawd I can't believe people are still doing this challenge... I almost beat it and then my laptop deleted everything and I had to start over, I quit though.... might try this one again, but I don't have any custom content. XD anyway good luck y'all with this challenge, its a HUGE pain in the butt! :D

Katalina: The Wiki says BV, but as I said, I don't have BV; I thought it was OFB too, but the Wiki's usually right about these things.

Lavaster: Yes, there's already another one. Yours seems different in that it requires raising a child, whereas the other (if I remember correctly) just requires surviving.

Also, your sim can't earn money(is it including by selling what you crafted?) until he/she gets cosmetic surgery in this challenge.

Lfact: That is correct, BUT the child can make money when they're a teen. It must be from selling items, though, not a job due to "the exhausting homeless life."

Yours is actually quite different in a lot of ways, no worries! But the original does have some explanations of how to set up your lot for this type of challenge if you are lacking various EPs. (Like BV for walking to lots, or how to arrange your seasons)

How do you make a sim sleep on the ground..? @.@ I have Double Deluxe onlyy

Just wait until your sim pass out.

Asdf I hate doing that.

Oh and how do you be a barista..? o-o Sorry I've never done it before. :b

You need the University EP. Then go to a community lot with a coffee bar and click "work as barista."

Okay, IS there a hack to let your sims pass out on a community lot? I didn't have an associated downtown so I couldn't find anyplace to earn money on my first day, so now I'm trying to save for the easel with my limited energy and it is a PAIN to keep going back "home" just so I can pass out there. Especially since I've spent DAYS in community lots and still only have $115.