It would also be just about the shittiest "value to your fellow man":"dollars spent" ratio you could arrive, even with conscious effort.
You would be far better off pooling money to buy a foreclosed hotel, and offering it at cost to the homeless via donated rooms. Hotels with solid occupancy metrics are very profitable absent constant capex for room improvements, designer toiletries, etc. Giving a hotel room would be effectively splitting the cost of the room, and just giving the homeless person 50% of the cash and the hotel 50%, at best.
As others have noted, advocating for improvements to the mental healthcare system would do far more good to domestic homeless populations. As would reforming drug laws (penal and rehabilitory), donating gently used work clothes for interviews, personally hiring them, or a million other things.
This blog is thoroughly emblematic of an "edgy idea" that is inexplicably engaging otherwise intelligent and well meaning people. There are people who have devoted their lives and run foundations to aid the homeless who are much better sources than the linked site.
ps - if you would like to actually help people, look at Haiti, South Sudan/west Africa, or Syria where poverty, war, and drought are causing far worse suffering. Consider donating to help orphans in areas of poverty. Consider donating to help preventable death from disease (dysentery/cholera, malaria, AIDS, chagas). Consider donating to help preventable suffering (dental/split palate, fistula, cataracts)... time is the only thing that prevents me from continuing.