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It is among Canada’s greatest puzzles: Why has one of the country’s richest, most beautiful cities abandoned its historic centre to scenes of abject misery—even as it absorbs $1 million a day in social spending?

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Vancouver is extremely good at feeding, housing and supervising the injections of the Downtown Eastside. But for all the money and attention here, there is little success at either getting the area’s shattered populace back on their feet, or cleaning up the neighbourhood into something resembling a healthy community.

Until that changes, say critics, Canada’s “poorest postal code” is only going to get worse.

“We’ve made it Fortress Downtown Eastside; easy to get in, exceptionally hard to get out of,” says Ernie Crey, president of the AREA’S Aboriginal Life In Vancouver Enhancement Society (ALIVE).

As Vancouver’s cheapest neighbourhood—and the site of most of its social and Aboriginal services—the Downtown Eastside funnels in vulnerable and low-income people from across Western Canada.

Once there, “quite literally, there are going to be people on your doorstep dealing drugs or encouraging drug use … and beyond that, they’re going to try and exploit you in other ways, like turning you out for prostitution,” says Mr. Crey, whose sister Dawn lived in the neighbourhood for 20 years before she was murdered by serial killer Robert Pickton.

ALIVE, which does not take government funding, is one of the most vocal critics of what it calls the Downtown Eastside’s “broken system”: Unaccountable non-profits, a general disinterest in tracing the impact of government funding, and a complete lack of any coherent end-game for the place.