If that's his response to homelessness .... then we should just strip him of all his wealth, pump him full of alcohol and meth, get the city police to beat him with a rubber hose and throw him out on the streets of Winnipeg and see how he fares on his own.
If he believes it's an easy problem to solve, then he should be able to figure out by himself how to get his life back together and get off the streets.