Ok...how much? I don't generally bet, but if you're going to give me money, I'll take it. Before you answer, you need to read up.
http://www.homeaid.org/homeaid-stories/69/top-causes-of-homelessness
https://en.wikipedia.org/wiki/Homelessness_in_the_United_States
http://www.nationalhomeless.org/factsheets/why.html
https://www.homelesshub.ca/about-homelessness/homelessness-101/causes-homelessness
These are just four out of hundreds of articles, all saying the same thing. If you read these and still want to make that bet, you let me know.
The first link, says this:
Homelessness is, in fact, caused by tragic life occurrences like the loss of loved ones, job loss, domestic violence, divorce and family disputes. Other impairments such as depression, untreated mental illness, post traumatic stress disorder, and physical disabilities are also responsible for a large portion of the homeless.
That's pretty general. Job loss? Gee how come? Family disputes?..What the heck does that even mean? And are you going to believe a link that doesn't even mention drug addiction? I don't buy that at all---and you shouldn't either. There is no dispute about that.
Third link is from 2009 and completely irrelevant now. it even says part of the reason folks are homeless is due to a lack of available jobs, this is not true today.
Your fourth link is from Canada. Ugh.
So back to my point, sure, those reasons listed above, that are not controllable--like a hurricane, or domestic violence(as the victim, not the perpetrator) are of course reasons why people are homeless. But I am standing by my assertion that there are a very large amount of people who are homeless because of the decisions they have made in life. Your links did nothing to change my position on that. They are essentially worthless--at least the ones I clicked---I can't click anymore since you don't even read your own info. So I would totally win my bet.
And again, the argument isn't that we shouldn't try to do something about this, but I'm telling you that your fantasy that somehow if you treat folks nicely they will be nice back is laughable and you will regret it. Ask anyone woo has been burned by a drug addict, or a thief. Its absurd.
ETA: And this is from your Wikipedia link:
34.7% of all sheltered adults who were homeless had chronic substance abuse issues
About 50% of people who are chronically homeless had co-occurring substance abuse problems
It's almost like you don't even understand what you are reading.