Thats literally what they did in Medicine Hat!
city staff found housing for one man, but he insisted on leaving to sleep under cars. Day after day, they’d search him out and take him back to his new home…“They did it 75 times, but they had the patience and they didn’t give up on him and, eventually, he ended up staying in the house,”
I found this part the most interesting:
it costs about $20,000 a year to house someone. If they’re on the street, it can cost up to $100,000 a year…“This is the cheapest and the most humane way to treat people,”