Boy, time sure does melt away when you're writing a daily blog and trying to build buildings. It's hard to believe that it has already been 7-8 years since I was writing incessantly about the merits of Toronto removing the eastern portion of its elevated Gardiner Expressway.

For those of you who may not be familiar, Toronto has an elevated highway that runs along the waterfront. It is old. Pieces sometimes fall off. Lots of water will drip on you. And so remediation works are underway. Several years ago, there was also a great debate that took place in the city about what should happen with its eastern leg. I even spoke at a Jane's Walk where I was, for the most part, not very popular.

The two options under consideration ended up being: 1) remove it and replace it with a grand surface boulevard or 2) remove it and rebuild it with a slightly different alignment. This second option was dubbed the "hybrid" option, but that was mostly political speak so that it sounded like some sort of generous compromise. You can think of it as the more expensive rebuild option.

City Council voted on these two options as one would expect. Councillors in the core of the city did not want an elevated highway running through their neighorhoods, and the Councillors and people in the inner suburbs -- who might use it for commuting -- were by and large more accommodating. Apparently there are somewhere around 15,000 commuters who use it each rush hour.

But here's the thing.

This vote took place in June 2015 and the thing still hasn't yet been rebuilt. So maybe it's not too late! Maybe there's an opportunity to save a few hundred million dollars between us friends. Also, if anyone is interested, I'm still available for controversial Jane's Walk presentations. One new idea I have is an elevated highway that runs through the inner suburbs and connects the best weekend brunch spots.

I just discovered a new alliance of non-partisan, non-profit resident and ratepayer groups in the Greater Toronto Area that have come together in opposition of what they see as "unregulated overdevelopment and the lack of sensible growth vision for the GTA." If you'd like to read through their public letter to the Premier of Ontario, Doug Ford, you can do that over here.

In it you will learn that the Toronto region is vying desperately for the title of the most densely populated place on earth by trying to compete with already established locales like the slums of Mumbai and Monk Kok in Hong Kong. One has to admire ambition.

But what is not clear to me is what exactly "sensible, balanced, affordable, and livable developments" should look like. Should we quash our low-rise "Neighbourhood" designations (the majority of our land area) and instead blanket the region with mid-rise buildings similar to Paris? This is one option and, by the way, Paris is far denser than Toronto (relevant reading here and here).

Or should we maintain our low-rise "Neighbourhoods" exactly as they are and simply reduce overall housing supply by limiting height and/or density at our transit stations? Is this the ask? I'm not sure. But this is a good question for city builders: What should sensible, balanced, affordable, and livable development look like? Is the 33-storey building that I live in sensible?

Alex Bozikovic of the Globe and Mail recently made a good point in one of his articles about how challenging it is to properly "placemake" when it comes to large-scale masterplanned projects. This blog post is not at all intended as a commentary on any one project, but I would like to acknowledge that, for a variety of reasons, places do often need time, layers of history, and some patina on them in order to really settle in. When you build big, it can be easy for things to end up feeling sterile.

It is also true that tastes can change over time (as we have talked about before), though you could argue that this change is driven by the settling in process. Spaces start to get rethought, reconfigured and recast, and that can make them more desirable.

But it's not just about time. What else is going on here that makes masterplanning so tricky? Four things immediately come to mind. If you have any others, please share them in the comment section below.

One, a lot of the old stuff that we love is now illegal and no longer possible. Here is a great example from Paris that I wrote about. But there are countless others. Another example from Toronto might be the corner retail stores that used to dot our residential neighborhoods. In my opinion, these are wonderful additions. They create urban vibrancy. But today they are generally legal non-conforming uses.

Two, great urban experiences often happen at the micro scale. Things like the perfect patio with a great view of the street and full afternoon sun. Or that intimate side street lined with beautiful homes. These are some of the moments that make cities great. But when you're masterplanning at the master scale, it is perhaps easier for more of these intimate details to get lost.

Three, any new community needs to be seeded. Cities and communities are nothing without people. And so what will be the anchors? What will bring people here? How are we going to animate its streets and public spaces? These can be tricky problems to solve and they often take time (and density).

Four, masterplanning likely equals fewer feedback loops. I recently came across this great line from Chris Dixon: "Composability is to software as compounding interest is to finance." Composability is the ability to mix and match software components. And the idea here is that open source software allows new software to get built on top of existing stuff (just like interest on top of interest). This way the world never needs to solve a problem twice.

I'm not sure what the pithy line should be for city building, but cities also compound. We are constantly building on top of the efforts of others, except when we're largely not, and we're designing a whole bunch of new stuff all at once, as is typically the case with masterplanned projects. This isn't inherently wrong, but building a community from scratch will always be more difficult than adding on to one that is already successful.