I have met
a few people who prefer to literally live on the streets and beg for money. In this state (frigid winters, hot summers) it is a choice involving rather harsh conditions. They were not your classical cynics. They were people for whom living at close range with other people (especially the sort of people one finds in shelters) was unacceptable / impossible.
I might choose to live on the streets rather than live in some of the shelters that are available. (Most of the homeless do not live in shelters, because there are not enough of them. Homeless, btw, doesn't mean literally "unsheltered", sitting in the cold rain. It means not having a home address. One may be sheltered and homeless.
I bet most cynics, followers of Antisthenes and Diogenes, did not opt to live in the streets of Athens, at least for very long. If they did, there was probably be an urban renewal program launched to get rid of them.
Diogenes, living in his amphora (a very large fired clay storage pot) might have been nuts, it's hard to tell at this distance in time. Presumably he was striving to make a large philosophical point. I've cited her before, I'll cite her again. Dorothy Day was a socialist, journalist, single mother who developed into a being a devout Roman Catholic. She started the Catholic Worker Movement (CWM). In some ways she was a cynic. Her calling, starting in the Depression, was to help the homeless and outcast people in the slums of New York. She didn't live in the streets, but she did live with the poor in the CWM's crowded, dirty shelters. She had virtually nothing.
There are probably similarities between the founder cynics and the CWM: The message wasn't "live in a filthy shelter with filthy people. It's good for you." Rather, their method was application of Jesus' command to care for the least of his children. The Catholic Worker lives in poverty in order to be able to carry out Christ's command.
Similarly, the two Prime Cynics probably taught people and lived their example. Diogenes would crawl out of his pot in the morning, wash up in the public bath (maybe), beg for some felafel and flat bread for breakfast, then head off to agitate the rest of the day, feeding whenever somebody offered him a handful of feta cheese and tabouli. He probably never needed to find a larger jar because of weight gain.