David Peter Allen, who goes by the street name Dexter, picks up what's left of his home and starts building again.

The Toronto man, who turned 45 last month, has lived on the street for the past two years, most recently in a green tent under the Gardiner Expressway. He's had to rebuild it four times, he says.

"We came back and it was totally shredded. Tools gone — stolen. Tent got shredded, vandalized," says Dexter.

He says, in this case, the theft and destruction is unusual as most of the community living under the concrete shelter of the expressway look out for one another.

More commonly, it's city workers who dismantle their makeshift homes and dispose of their possessions in what the homeless and outreach workers call an expensive game of "whack-a-mole."

Allen says all his worldly possession are packed on a cargo wagon and a couple of bikes. He'd rather take his chances living on the streets than go to a homeless shelter, which he considers less safe. (Philip Lee-Shanok/CBC)

"You go out, come back and everything's totally gone. Truck and the cops. They come by and take everything — a couple of trucks, sometimes a couple maybe a dozen guys — and when you come back it's like you were never there. Everything is gone."

And just as has happened under the Gardiner multiple time this summer, the inhabitants return with tents and possessions.

"We pack everything up, go away for a day or two. We come back. Rebuild," says Dexter.

According to the city's Transportation Services, staff have cleared the encampment under the elevated portion of the highway at Spadina Avenue on four occasions during the summer.

Each time, the cost of clearing out these encampments and cleaning the area up is about $3,500, all of which is covered under the department's yearly budget allocation.

Greg Cook, an outreach worker for Sanctuary Ministries Toronto, a charity that helps those in marginal situations, points to the affordable housing crisis as the reason such tent cities exist.

"It's awful, but people need to sleep somewhere," says Cook, adding that affordable housing is not being built in Toronto and rents have skyrocketed, especially in the downtown core.

"If you're on Ontario Works or on disability, a pension or you're making minimum wage, you probably can't afford much," said Cook.

Greg Cook, an outreach worker for Sanctuary Ministries Toronto, says the money spent taking down tents under the Gardiner Expressway could be better spent on low barrier respite centres. (Supplied by Sanctuary Ministries Toronto)

Meanwhile, rooming houses — once common in some downtown neighbourhoods along Jarvis and Sherbourne streets and in Parkdale — are disappearing.

"The landlords are able to make a lot more money if they are able to kick people out and then convert them into condominiums or ultimate luxury rentals, so that's happening," he said.

And, Cook says, the city's shelter system is under stress.

Dexter says he had a basement apartment, but the landlord targeted him for eviction for hoarding and causing a fire hazard.

"There's no housing for me that I can afford. I don't have enough from (Ontario Disability Support Program)," he says.

As for staying in a shelter, Dexter says he doesn't feel safe.

"Anything of sentimental value will be stolen from you in the first week," he says, adding that he prefers life on the streets.

"You live free. If you go to a shelter, it's a dictatorship. You gotta do this, you gotta do that."

Cook thinks the money spent on tearing down tent cities should go to low barrier respite centres, which have fewer rules than shelters.

"That would be an immediate fix," says Cook, who points out the median age of those who die while living on the streets is 48.

And he says improving conditions in shelters would help give those living in tent cities an alternative.

"If they are under-staffed and overcrowded then it also makes it even less likely people are going to want to stay there," Cook says.

"If they were better funded, then they're going to be safer places to sleep."