To my understanding. The practice is not owning a home. Not having a fixed home. In Sri Lanka there is a few monastery that was given to the Sangha by government.
But at the same time it’s also about your mind. Not living in what is not yours. Letting go.
The practice of living physicaly in what is not yours. It’s training the mind to have no attachment. The practice of not fixed abode. Is for the same purpose.
So as anagarika
The real homelessness would be crashing at random guest houses.
If it’s a van or house and it was given and it’s used long term. That is not truly practicing being homeless. It creates attachment.
Nowadays monks itself stay years at one community. But in time of Buddha they kept roaming around without a fixed abode.
But only in the rainy season they stayed at one place. Sometimes lay supports them and makes the place just for the rainy season.
In Sri Lanka there is a tradition of monks that they keep changing monasteries after a few months. To the ancient practice of not having a fixed place.
There is the advantage of not attaching to the laypersons of each monastery. Besides that you won’t have a fixed Kuti.
Here in MN 140. Buddha asked to stay one night?
I have heard that on one occasion, as the Blessed One was wandering among the Magadhans, he entered Rajagaha, went to the potter Bhaggava, and on arrival said to him, “If it is no inconvenience for you, Bhaggava, I will stay for one night in your shed.”
“It’s no inconvenience for me, lord, but there is a wanderer who has already taken up residence there. If he gives his permission, you may stay there as you like.”
Now at that time a clansman named Pukkusati had left home and gone forth into homelessness through faith, out of dedication to the Blessed One. He was the one who had already taken up residence in the potter’s shed. So the Blessed One approached Ven. Pukkusati and said to him, “If it is no inconvenience for you, monk, I will stay one night in the shed.”
“The shed is roomy, my friend. Stay as you like.”
The owner normally can say how long you can stay. But the practice was not to stay long.
A cave is a good place. But even then you don’t have to make it your fixed abode. Tent can be used. Just the tent had to be given. You decide your practice. The days , months. How extremely you can take it.
The key is not creating attachment.