Homelessness, for the insane, is not a choice as it is unreasonable to consider them responsible for what they do.
Homelessness for the sane might be a choice. Some people choose not to become a wage slave in order to get money to give away to another man in order to live on this earth that rightfully belongs to God, not man.
There was a time, quite a while ago, in many lands, when the idea that man could own the land was considered sacrilegious. Then, it was impossible to be homeless because you could live on any piece of land that was not already occupied by another man.
But, that was then and this is now. Now, in our "civilized" society, all land "belongs" to some man or men. The vast majority of this already owned land is owned by men who live somewhere else. They do not need the land themselves to live on, or to farm on to feed their families. The land, for them, is a source of income.
To live on "their" land, you have to pay the owners some money. If you do not have enough money, and have no means to earn enough money, you will be homeless out of necessity not choice.
Even, if you own a car, you could still end up homeless because the rich men who own most of the land have influenced the politicians, whose re-election campaigns those rich men pay for, to pass laws making it illegal to live in your car, or sleep on a bench in a public park, or crash on the beach, etc.
American society considers you to be irresponsible if you do not line up with the other copper tops and agree to be a wage slave for the rest of your life in order to make enough money to pay to live on land which is more often than not owned by rich people who already have more money than they could hope to spend in one lifetime.
In this age, America does have homeless shelters where those without money to pay other men to live on God's land can get a roof over their head. But, I don't know if I would call that a home or a choice. In many ways, shelters are a peculiar sort of prison. To sleep there, you have to agree to be told what to do and where and when to do it. Also, they put you and your belongings out at dawn and you cannot come back until dusk. And, even then, America has far more homeless than shelters anyway.
Luke 9:58
And Jesus said unto him, Foxes have holes, and birds of the air have nests; but the Son of man hath not where to lay his head.