I’d do it. It’d be easy money. I’d use the library internet to search freecycle and craigslist for free stuff. I’d use that free stuff to barter with other people for food or clothes. I’m pretty handy with home projects. I could easily score room and board for working around a church or something.
Sorry, I think the survivability of this as a fragile female wheelchairborn gimp is pretty shitty. I would be capped for my painkillers alone.
Food should be easy. Any time the topic of the homeless comes up, someone always has the same “Some ‘homeless’ guy asked me for $5 and when I offered him a steak dinner he said no!” story.
I’ll be the homeless guy eating all that food people are offering!
I would do it as long as it was not the nearest US city. I would definitely not make it through the winter.
A southern city and I would give it a whirl.
So, I can go to a bar the first night, explain the situation to whichever guy seems the most appropriate, and offer him a couple hundred grand a the end of the year if he’ll let me live with him? Damn, this is going to be easy money. Hardest part of this whole thing is going to be convincing my husband that it’s a good idea.
From the linked list, it looks like I’ll be going to Houston. It also looks like they have a very well organized homeless coalition, so there are definitely services to access. Skald - what are the rules for accessing transitional housing? According to the feds, being enrolled in a transitional (or hell, even a permanent) housing program run by a homeless organization paid for with HUD dollars still qualifies someone as homeless. For me, I’d have extremely low barriers to housing, making me an ideal candidate for such assistance. I’d be willing to bet I could be living in paid-for housing inside of a month, and still maintain legal homeless status.
I’m in.
Oops, I’m out.
Certainly, especially with a guaranteed payday at the end. Counting the monthly stipend, it works out ~28K/day. One could take a lot of physical discomfort for that kind of money. And really, that’s all you’d be facing. Where do I sign up?
I’d think that would count as taking a loan against the prize money which is forbidden.
Also, if some strange woman in a bar asked to move in with me for a year starting that night and she promised to give me a hundred thousand bucks in 2013, I’d assume she was planning to harvest my kidneys.
Uh, this has been answered at least twice, including the OP. 
A data point - there are homeless people in every Canadian city, and they don’t all die each winter (I rarely hear of homeless people freezing to death, and your chances of that go way down if you aren’t chemically altered and pass out somewhere dangerous). In places where it gets cold enough to kill you, there are resources to keep people from freezing to death.
You mention day labour, Skald - as an office temp, could I work shifts in offices? That would make it a gimme for me.
But do none of them die?
I don’t see anything in the OP that says you can’t access transitional housing. But I also don’t see anything that prevents your handler from approaching the administrators responsible for said housing and telling them that you’re not truly homeless, but rather are essentially playing a game with a $10M payoff for you and thus taking a room from someone who doesn’t have the access to, among other things, free prescription meds and bodyguard.
I’m going to say that’s not in the spirit of the competition. Day laborers in my experience are paid in cash each day and do heavy manual labor. I think the handler will rat you out and the billionaire is going to shrug, “Yeah, we’re done here.”
Also, saying you rarely hear of homeless person freezing to death implies that you sometimes do. No?
Yeah, as I mentioned previously, if you pass out in a snowbank, chances are you will die. Since none of us are likely to do that, we’re probably good. 
So, no temping, eh? Have to think about this then.
I’d give it a shot.
I do a lot of camping and the longest trip I’ve been on was three weeks, and it wasn’t as rough as I thought it would be. So I’d consider urban camping for a year an adventure.
I’d probably head out to Vancouver because it wouldn’t get that cold during the winter. I’d definitely bring rain gear obviously. Portable stove, pot. Extra pair of shoes, socks, lots of socks. Extra pair of clothing.
I don’t know how close Stanley Park is to urban Vancouver. But if close enough I would probably end up squatting there so it would feel like one long camping trip. Since I’m there I might as well harvest psilocybin then seek out the college crowd and turn a profit.
I would spend my time volunteering in soup kitchens, visiting libraries, scam my way into YMCA someway in order to take showers. Look for an abandoned building I could get into and squat there if necessary.
I think I’d have some lows during that year, but otherwise very do-able.
I’d do it- though where is the nearest US city to England again? Somewhere cold, I’m guessing. I have no family in the US, or friends that can be even vaguely described as close.
Assuming all the visa stuff was sorted so I was all legitimate, I’d take up busking, as a juggler/hula hooper and see how well I did. I’ve lived out of a backpack for 2 years before, in different countries, doing fruit picking, and couchsurfing- and I reckon I could get enough money per day performing to find a cheapass backpackers. Plus the juggling scene is pretty friendly- I’m fairly sure I’d be able to find a few people through that to let me sleep on their couch, friends of friends, so it should still be within the rules. This sound legit?
If so, yeah, where do I sign?
Two questions:
Am I allowed to make use of places like homeless shelters and soup kitchens?
Will some provisons be made for taking care of my home and possessions while I’m away for a year?
Nope not leaving my little girl for an entire year, no matter how much I get. I know, “Just think of all you can buy her!” but it’s not worth it to either of us.
If the “handler” is going to dick me over for going to a shelter, I assume the rich guy is going to seek any loophole to avoid paying out. Which changes my opinion of the bet quite a bit.
I would do it. I think I 'm creative and resourceful enough to do it.