So if I can find some lonely guy who wants a delightful companion (hey, I WOULD be delightful if I knew I had $10 million on the way) in exchange for room and board, that’s allowed? That doesn’t sound very hard.
Five million is my minimum. Don’t tell the billionaire.
Many of the actual homeless manage to survive despite being chemically active and/or mentally ill. If you are neither of those things, you should be able to come through this with relative ease, since you will be clean and rational enough to take advantage of services they will not or cannot. You also, presumably, won’t be spending what money you do get on booze or drugs.
I’ve been homeless before. Sign me up.
I think prostitution counts as day labor.
But I’d be wary of this, as you’re putting yourself at the guy’s mercy, especially when you’re in his house alone with him and out of your handler’s sight.
You have the same resources as any other homeless person: libraries, churches, shelters, etc. I don’t know what Phoenix homeless shelters do about people doing the day, which is obviously more dangerous than during the night.
What’s your plan? Bear in mind that at the very least you’re not doing this in your current city, and depending on how extensive a network of friends and family you have, you may well wind up someplace like Buffalo during the winter or Phoenix during the summer.
I’d do it. And I wouldnt even try to “cheat”. Like others have said I’d consider it a chance to hike/walkabout/have some time for contemplation. I suspect many homeless folks problems are due to addiction, mental illness, physical illness, lack of education or intelligence, and virtually ZERO basic resources to fall back on. In this scenario I would have none of those problems (or at least they are greatly reduced). Now, I might decide 3 months into a Chicago winter to say “fuck this shit”, but given the chance at 10 milllion I’d take a shot. Don’t get me wrong, being homeless has got to suck for people who don’t WANT to be and DON’T know what each day brings. But IMO this scenario ain’t remotely like being a “real” homeless person.
Well, the handler might be a lonely guy…
Win-Win!
I live in Minnesota, so I know I couldn’t do this in my current city.
If the selected city had anything substantially milder than a Minnesota winter, then yes.
I’d write a book about my experiences, which is how I’d sell it to my family. I’d surprise them with the $10 million.
I’d pick a city where I could stay in the desert or woods. I’ve read Tuscon has homeless people in the nearby desert. Albuquerque might be another choice.
I’m confused about the city-choosing algorithm. Is it:
Choose largest US city. Is it disqualified due to friends/family? If no, you go there. If yes, go to:
Choose second largest US city. Is it disqualified due to friends/family? If no, you go there. If yes, go to:
Chose third largest US city…
Then, are you obligated to STAY in that city? Or are you only obligated to never visit a US city disqualified by friends/family? Because if I were dropped off in New York, I’d probably hike the Appalachian Trail. And by that, I mean hiking, not boning a chick from Argentina.
You got it.
You’re not obligated to stay in the city, so long as you don’t visit any place with friends & family about. (And presumably trying to lose your handler is going to get you disqualified.)
How long are you going to stay in NY before you beginning walkabout? Let’s take as a given that you don’t have access to your savings, just the monthly pittance and whatever you accumulate day laboring, begging, or stealing before you hit the, um, Trail.
I’m not sure how exactly I’d go about this (probably use Craigslist at a library), but I could probably find a job as a live-in nanny or housekeeper or something instead pretty easily as long as I could do it right away, and not later after I looked unkempt. I’d be cheap (room and board only) and undemanding like an illegal immigrant, but with better English.
In this scenario, since you have the guy watching you and don’t have to worry as much about your safety as you would in reality, it seems that nonthreatening-looking women really have an advantage over like a big burly man who nobody is going to want as a nanny or as a recipient of sugar daddy or Captain Saveaho services.
It’d have to be Boston. I’d die in Boston.
Naw, I wouldn’t do this for love or money.
Been there and done that for a lot less.
No prob.
Mika, it’s not the nearest big city in which you haven’t friends or family; it’s the biggest such city. LA, Houston, Phoenix, San Antonio, San Diego, Dallas, San Jose, Jacksonville, Austin, Charlotte, and El Paso are all ahead of Boston on that list. (I’m going by the list I linked to earlier, which ranks cities by their base populations, not by metro areas.
Czarcasm, best not say that to the billionaire. He’ll add conditions to make it harder for you personally. 
I said yes. Weather would be my major concern and since I have friends in NYC according to the Wikipedia list of US cities by size I’m heading to LA.
As other posters have said - being not mentally ill is a huge advantage and some creative packing and preparation will put you in an even better situation. You’re also insulated from some other downsides of being homeless - the feeling of failure and hopelessness. You chose this for a reason and it has a deadline. I could spend the days reading abandoned newspapers to plan for the new home we’d be moving to upon completion!
I want a codicile to his will though - if mr. Rich and insane kicks off before the year is up I want my money guaranteed!
I’d have to go to Chicago. For that, I’d want $2,000,000. If I got to pick a city with better climate (e.g., Los Angeles, San Diego, anywhere in the Southern half of the U.S., really), I’d do this for $1,500,000 (or maybe even less).
So your handler steps in before you’re criminally assaulted - is that guaranteed? I deal with the homeless all the time as a librarian - I’m not worried about freezing to death, I’m worried about getting raped and stabbed to death. If you’re guaranteed a certain amount of safety, sure.
Assuming I’m not hiking, my daily plan would be simple: Head for the public library. Sign up for the one hour of computer use. Sit in the warm clean comfortable library chairs and read, read, read. Magazines, books, newspapers–I’ll get back into reading the newspapers since I wouldn’t want to waste my one hour of internet reading the news online like I do now. Cutting down to one hour online a day would probably be good for me.
This would be utter bliss. I’d do this right now if I didn’t have to work for a living.
The trouble comes when the library closes. How close is the library to the mission/shelter/whatever? Gotta plan my route. And it will be raining and snowing, what a pain. Then sleeping. The problem isn’t dealing with homeless people per se, the problem is dealing with people who have issues so severe they have ended up homeless. Lots of people have issues and lose their house and can’t afford an apartment, but they have friends and family that are good for a couch, or staying in the trailer out back, or what have you.
It seems to me accumulating free food and a free bed every night takes a lot of work. That’s going to seriously cut in to my library time.
Can I choose the city? I’ve never lived in NYC, but I wouldn’t want to spend a winter there homeless. San Diego? Los Angeles? Miami? No sweat. Well, yeah, I’d sweat, because it’s warm in those places, especially in summer, but … hell, you know what I mean.