Homeless Challenge:
Okay, I made this challenge, as a bit bigger challenge than the Severe Poverty Challenge, enjoy it :D

Start out by making a sim, only ONE sim.
[Everyday clothes should preferably have black or brown-ish colour]
Move the person into the biggest empty lot you can find.
You CANNOT have both mooch and kleptomaniac trait.

Buy a tent or bench, and a picnic basket. (Cheapest you can find, that fits the outside)
Use [Familyfunds Familyname 200]
(You have to turn the Testingcheatsenabled true on first, turn it off afterwards)

When you have earned enough money to build a 3x3 squares house, (you don't need wall painting or floor), and 400 simoleons you may take a part time job.

When you have got a 8x6 fully furnished house and at least 5000 simoleons, you may get a job from the:
Criminal, Military or Law Enforcement.

When you have got a husband/wife you may go for any other job but Medical and Science.

After you got your first child, and max out your logic, you may go for Medical and Science.

[HELP FOR BEGINNERS]
To earn money at first you can use fishing, kleptomaniac-ism, farming or mooching.

can you buy a tent without first going on vacation? like, in the home neighborhood?

No, I don't think that's possible...

BuyDebugMode On, maybe.

I know for those who don't have WA there's a mod that makes the tent a buyable item with the rocks.

Was doing this challenge, got a fully furnished 8x6 and 5000+. Completely forgot about the job restrictions and got a job in the culinary track. Oops.

are you sure that doesn't require world adventures? it seems to me like the tent wouldn't function correctly without the animations and everything..

I only have the base game and it serves its purpose.

It has no animations. They stand in front of the tent, change into pjs and then vanish into it. When they come out things get sort of glitchy. They are invisible. Now the times I've had the tent be the only sleeping place on the lot when I've had them travel to another lot through map view they've reappeared. Also resetsim fixes that issue.

Personally I think it's easier then a bench when you have to constantly tell them to nap. Anyway, when they're invisible you can still make 'em do stuff, you just can't see them.

isn't that illegal?

To be quite honest, I'm confused by your question.

It's a mod. I've seen a few of them that alters already present items in the games. If this is what you're questioning the legality of, I only think the company that makes the Sims would care if someone was selling these alterations for money and they were not getting their cut. Sort of like fan fictions and art.

Now is it considered cheating in the game? That's up to you. I just know a bench was a pain in the butt to deal with.

And just looked at the mod again. It states its for WA but it works fine for me in the base game with issues I've stated previously.

I started my own homeless challenge somewhat similar to this one. But instead of having them buy a bench, they had to sleep wherever a bench was already available or pass out on the ground. And to make the game harder, they were not allowed to sell any rocks they managed to find. I also had them constantly foraging for harvestable items or lingering at picnics for some free food. :3

They did end up being stinky for the first week or so though, because I found out swimming doesn't bring hygiene back up in TS3.

Once he was able to have a roof over his head, with no incomplete room or Darkness moodlet, he could start trying for a job. :D

I had a homeless sim once that lived on community lots like the gym or library. She eventually became friends with a rich guy and mooched off him. She had to keep asking him if she could sleepover but she ended up staying there most of her life.

If you have Island Paradise you can get a tent.