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Sims 2: The Homeless challenge

(updated version here)
Note: I wondered if I should include this challenge on the site, because it sounds so much like the "poverty challenge". Although, after playing it I think it really is like the poverty challenge (only 10 times as hard). I realized that I'm suppose to put my favorite challenges on here. It wouldn't be fare if I didn't even mention this one. You can try this one, or the poverty challenge; but try both. See which is the hardest.
Warning: This is really hard. As in, mind-blowingly aggravating. It will also be extremely hard, if not impossible, to do this without expansion packs, since your options for earning money are much more limited.The rules were created for realism, not sanity.

Basic synopsis: You are one of the thousands of homeless roaming the streets. With little to nothing in your name, can you save up enough to buy your own little lot of land and finally leave the streets for good?

Setting up: Start off with one Sim. Give them the Fortune aspiration, then roll for personality any way you wish.

The Home Lot:You found this abandoned lot on the corner of nowhere as a safe place to sleep and sometimes store little tidbits. You dream about someday owning it…Buy any size lot, then reduce funds to $100(You’re poor, remember?) You cannot have a house or build anything on the small lot, including swimming pools, etc. In fact, the only thing you are allowed to do in build mode is flatten terrain.

Objects:-Only small, non permanent objects are allowed. Placing anything else on the lot will alert the police to the fact that you are hiding there and might get you thrown into jail for trespassing. -No toilets, sinks, stoves, baths, or even phones, etc.
  • (*EDIT* Thank you to Engram for bring this to my attention. Non-BV players are allowed to have one phone, but may not use it for anything other than taxi rides.)
In fact, for most of the challenge the only objects that will even touch ground will be the newspaper or the bills. Obviously, without a phone, you are also not allowed to hire a maid (to clean what?), exterminator, etc. You’re homeless, you don’t need it anyway.
If you have Nightlife, only six tiles worth of portable objects will be allowed in your inventory (so for instance, if an object takes up two tiles, you only have four tiles worth of space left). If you do not have NL, you are allowed to place the six tiles of portable objects on the ground.
Be reasonable: a large statue, though only taking up one tile, is most definitely not portable. An easel, however, is. And a tent is not considered portable for our purposes.
A few objects seem to be ‘gray area’: the small telescope is considered portable, however, it may not be worth it (it takes up quite a few tiles).
The grill is obviously not portable, and neither is anything that causes fire, really. The police would immediately notice you and evict you.
Newspapers and bills do not count towards the 6-tile limit.Money Matters You cannot take a job because of your shabby appearance, so the newspaper is essentially only good for the crossword. After that the only use for it would be as a paper plane. Do not underestimate this!
Since you are essentially homeless, very few “fun” restorers will be available to you right from the start. Use your resources wisely. The bills must be paid even if you do not actually own the land. They will represent your other living costs, such as taxi fares (which do not exist in Simcity for some odd reason).
Needs As you may have assumed, your survival depends upon using the community lots well.
Most stores will have sinks/toilets you can use, and some will also have food (you may also have to pay for this, so be careful!).
Restaurants, coffee shops, and OFB businesses(if applicable) are also allowed, so use them to your best advantage.
However, the player-owned businesses cannot hire you.
As for sleeping, you are not allowed to use hacks to sleep on community lots, and can only sleep on the floor at your home lot.
You cannot create an all-in-one community lot specifically for this challenge.
Finishing the Challenge:
The basic goal of it all is to earn $20,000 any way possible.
Work as a bartender, barista, DJ, anything like that
You may also (as mentioned) use the easel to sell paintings.
You can move in and/or sleep with whoever you wish (except for playables), but no hacks are allowed in the process…and remember, you don’t have a phone or computer, so consistent communication with a townie is very difficult.
You may move one person in only, and cannot use the Ask... interaction about money.
If a townie does move in, they MUST quit their job (AKA get fired for not going).
You may not control the townie.
You must bring the townie/NPC with you at all times (if you go to a community lot, you must bring them.)
No dates or outings.
Kids are not allowed out of concern for player’s (remaining) sanity.
After earning $20,000 you can apply to be the owner of the abandoned lot you sometimes haunt (AKA your Home lot), and the challenge is over.
  • If your poor Sim dies, you do have ONE grace quit without saving in case of a situation impossible to survive as a hobo in. That's all. Once you get over that, you lose the challenge.
  • If you get turned into a vampire, you are allowed to quit without saving. If too late, you are allowed to cheat to return to normal, however, both count as your one grace opportunity.
+100 for every friend you make
+500 additionally for every love
+1 for every aspiration point
+1000 for every $10,000 (so at the end, if you finish, you’ll get 2,000 pts automatically)
-100 for every enemy
-10 for every day that it takes to get to 20,000 (if you finish)
Expansion pack extras:
No cell phones
No dates.
Obviously no OFB businesses.
The OFB creations are otherwise considered GREY AREA, banned or allowed according to the player's wishes.
The stations do count toward the inventory max, however.
No gardening.
In Seasons, arrange the seasons so that there is no Fall.
No digging for treasure.
Sims 2: The Homeless challenge
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