I started a new sim a few days ago, and it was super fun so I thought I would share.

Make the sim of your choosing, with any traits. Move that sim to an empty lot, and proceed to get rid of all of his money. I bought a few rather useless decorative items and tossed them into the family inventory, and a bicycle that I allowed my sim to keep. Then send them out on the town!

Don't build anything on the empty lot. Pretend it is not there, your sim is living off the town now.

Similar to the "Living off the Land" challenge (which looks great, it will be my next one!) you can fish, gather rocks, and harvest wild plants and sell the bounty. However, you can not garden (you are homeless, where would you do it?) and you can not send rocks to be cut/smelted/etc as you would need a home with a mailbox to do it.

If you earn enough money you can buy a guitar and start working for tips, but no regular jobs!

You can keep them homeless, or allow them to move into a house if the save up enough money to purchase a new one, but no building on the current lot.

It is a definitely challenging at times, and often hilarious! I would love to hear the stories if anyone else tries this.
:lovestruc

Ah, I think if you make a sim, move them into an existing family household, and tell them to move - but pick the 'kick out' option, they're actually living on the streets, with no home. :]

No, the game finds them a place to live. They go anywhere.

Aw, darn. Never used the option, so I was hoping. :P

As buying a guitar and busking for money is allowed, is buying an easel and painting allowed?

Just out of curiousity, where does your sim sleep?

I haven't tried this challenge yet, but it sounds like fun. As far as sleeping goes, I once was able to have by sim nap on a lounge chair at the local pool, so it's possible.

And you could even give your sim the Mooch trait which could allow them to beg for change on the street - for the full effect!!

The easel would have to be placable on a community lot. I have not tried it actually, I will have too. So if you can carry an easel and drop it on a community lot to paint, sure! You can't place it on your home lot, because you have to act like it is not there.

You can take naps on some community furniture, or run your sim into exhaustion and let him drop where ever. I tend to do the later.

ok sounds fun started it where do they shower and go to the bathroom?

A number of community lots have bathrooms, and one of the pool lots has showers. My sim has taken a few sponge baths in sinks as well.

yeah I figured it out she goes to the gym by the park where she plays for tips it has showers, toilets and lounge chairs and is just a step away from park

Well, I kicked out my sim because he couldn't afford a house but he ended up living in a house that was worth over $100000!!!! I was just kind of like what the heck just happened. Then my other sim that I kicked out moved in with another family that had like two kids or something. So it does not make them live on the streets but instead gives them money out of thin air that they use to buy a house.

Ohhhhhhhhhhhhhhhhhhhhhh I HAVE to try this... Thank you for sharing it! *cackles madly and runs off to go try it*

wow this sounds like so much fun! Kind of like the poverty challenge, but more like the hobo challenge
The question would be, how is this scored, and when does the game end? What about kids, etc.

so basically buy useless decorative items and a bike, keep the bike and go be a hobo Sounds good to me. this will make for an interesting story line

good traits to have, Angler; Shmooze; kleptomaniac.

This isn't challenging, this is how I NORMALLY play, because the amount of money you start with isn't actually enough to buy a house worth crap anyway, and as crappy furniture is actually harmful to your sims in TS3, you are better off doing without.

I normally play along the same lines. The Sims get a good bed and fridge. They go to the book store to skill build and use the bathroom until I can afford the good shower. They wait even longer for their own unbreakable toilet. I do normally buy them a small house though, so this would be a deviation for me.

AH I cannot wait to try this....I've been wanting to do something related to being homeless/a hobo ever since I got the game(:

Sounds awesome!

That sounds cool. Gonna try it out right now:D

Just a question, I am trying that challenge right now and when I let my sim pass out, they only pass out for a few seconds and get up right away... all I can do is take naps.

Is that normal or am I just missing something?

Ciane - There is a painting easel in the museum in Riverview, so you could use that.

I'm gonna try this one; I wanted to do something similar with Lucky, but couldn't quite get the hang of it. 'Course, that was when I first got the game... but whatever lol. *goes to play*

Okay, I've started up my challenge, and yeah, energy has got to be the hardest thing about this challenge. Lately I've been having my Sim take several naps consecutively, since she'll only nap for a couple of hours and then get up. I'm working on making friends so she can "spend the night" at one of their houses. That would be much better, lol!

This challenge is so fun. =]
This would also be a really cool challenge when a seasons-style EP comes out, then our hobo sim will be out on the streets during a blizzard.

ROFL That would make for some funny stories!

Can you get a part-time job?

I am doing this challenge!