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The City of Toronto is working hard to deliver more housing. Only one thing stands in its way: the City of Toronto. That’s the conclusion I’ve come to in watching the Housing Now initiative work its way through the planning process.

Housing Now is a pet project of Mayor John Tory meant to address the city’s housing crisis. And yet, Housing Now keeps running into city-planning constraints that verge on the absurd – and giving up. This isn’t crisis planning. It reflects a status quo that badly needs to change.

In one corner, you have CreateTO, in charge of the city’s real estate. Its goal here is to build as much housing as possible, some at market rate and some subsidized. The objective: big and tall. In the other, you have the city’s planning policies, which regulate the scale, form and placement of buildings. Usually, these say: not so big and not so tall.

There’s a balance to be struck, and it’s always complicated, because Toronto planning rules are contradictory and inconsistent. This tension is usually resolved through negotiation. But not here, because city planners are sitting on both sides of the table. CreateTO and city planning “are working as a team to move these forward,” CreateTO communications director Susan O’Neill said this week.

This explains what’s happening at 50 Wilson Heights Blvd., a parking lot in the Downsview area by the Wilson subway station. It’s big, and the Housing Now project calls for 1,464 units. This is about a third less than a private development of similar scale, on a public school site at Bloor and Dufferin streets, that is nearing approval.

Why so few? And why is the tallest Downsview building just 16 floors? Because this fits the city’s 2015 plan for the area. “We have to work with the regulatory framework that’s in place right now,” Gregg Lintern, the city’s chief planner, said this week.

But that framework will soon be obsolete. It’s shaped by the Downsview airport next door; tall buildings are forbidden to protect flight paths. But aircraft maker Bombardier has sold the airport; it will move its aerospace operations to Pearson Airport. A spokesperson confirmed to me that they plan to stop flights at Downsview no later than 2023. And “when Bombardier leaves, the right to operate the airport goes with them,” said Chris Eby, who is leading the redevelopment project for Public Sector Pension Investment Board.

PSP will soon start a huge new project on the airport lands – which will bring planning changes, and also make the city’s site more valuable. Yet CreateTO is squandering its asset now.

When I put this point to Mr. Lintern, he countered: “We’ve been asked to deliver Housing Now, not Housing in Five Years.” Fair point: This is a crisis.

So why isn’t the city planning as though it’s a crisis?

Take the Housing Now project at Warden subway station. It has a preposterously low density of just 466 units – three smallish buildings – on seven acres. How many deeply affordable units could the city get here if it doubled the scale? Tripled it? How much good could this public asset do for Torontonians?

Another project, going soon to City Council for approval, is by Victoria Park subway station. It’s a perfect spot for housing in a city that claims to care about reducing its climate effects. There are mid-century apartment towers all around it, one to the south reaching 18 storeys. Yet the city is making a development proposal for … two towers of 23 and 11 storeys. Why not higher? Why not more?

It has to do with urban design, the art of what buildings should go where and how they relate. Mr. Lintern argues that the city “has learned a great deal” in recent years about creating livable communities. Fine in theory, and this is important work for city planners.

But there are glitches. The new Victoria Park buildings sit near an area designated as “neighbourhood,” and so they step down toward its edge. Even though the nearest edge of the neighbourhood is an 18-storey building.

This sort of thing gets wonky. But it doesn’t have to; the city writes the rule book. If City Council so chose, CreateTO could blow up planning regulations and propose much bigger buildings on each of these sites. Take the resulting revenue and serve people in need.

Think bigger: The city could expropriate land. It could close streets and put homes on them. It could build towers with zero parking, as the Squamish Nation is now doing in Vancouver. The city could be visionary.

Why isn’t it? The planners will point you to the City Council, and councillors and the mayor talk about “good planning.” It’s a circle, in which nobody takes real responsibility for the big picture.

And the big picture is scary. Toronto will add a million people in the next 25 years, according to projections by city consultants. Yet the Official Plan, passed 13 years ago, only envisages new homes for about half that many.

Toronto needs housing, and it’s in trouble, now. It’s time for the city to start acting like it.