I have a friend in town visiting me from New York this weekend. And since today was such a beautiful day in Toronto, we decided to spend the afternoon on the Toronto Islands–Ward’s Island to be exact. The islands are such an incredible amenity in the city. I try and go as often as I can during the summer. It’s my Central Park.

But in addition to parks and beaches, many people also live on the islands. There are 262 residential properties across the archipelago. Below is what a residential street looks like. There are no cars allowed. It’s a gorgeous place.

But if you want a house on the Toronto Islands you have to get on a waiting list. There only 500 spots and it’ll probably take you about 30 years before you get to a meaningful position on that list. But even then, you’re only buying the house. The land itself is on lease.

But if we didn’t regulate, the islands would be a very different place. 262 homes is not a lot of housing. In fact, it’s less than most of the new condo buildings going up downtown. So it’ll probably always be a heavily regulated market.

In addition to having an incredible mountain just 12 miles away, the town of Jackson is also a really cool place in its own right. It’s a cowboy town with endless wilderness all around it. But since it’s such a big tourist destination, the town is filled with great restaurants, art galleries, and the obligatory real estate brokerages trying to sell vacation properties.

Here’s what the town looks like from the top of Snow King (the in-town ski mountain). Photo credit: David Stubbs for the New York Times.

But from a land use standpoint, I also find the town really interesting because of its network of fine grain alleys. Here’s a picture of Gaslight Alley. For those of you who are regular readers of this blog, you’re probably aware that I’m a big supporter of laneway housing in Toronto. I think it’s a hidden opportunity. It could be another—more intimate—layer to the city.

Today, building a laneway house is virtually a non-starter with the City of Toronto. Whether it’s issues of utilities or the fact that laneways don’t easily accommodate service vehicles (maybe we need smaller service vehicles), the city has a litany of reasons for why they just won’t work.

One of the things I’ve always found funny about San Francisco is that, despite being a bastion of liberalism, it’s a city that’s incredibly anti-development. From the outside, it seems like a city filled with NIMBYs. Doesn’t that seem odd given its reputation as one of the most progressive cities in America?

Of course, many would argue that part of the reason so many people love San Francisco is because it’s done such a great job of preserving its history. And don’t get me wrong, I think that’s important. But as I’ve argued before, development should be about a balance. We should be looking to the future, while not forgetting the past.

Let’s put some numbers to this discussion.

According to Atlantic Cities, San Francisco has produced on average 1,500 new housing units each year over the past decade. Seattle does about 3,000. And in the Greater Toronto Area, we’re probably around 30,000. I’m not sure if the Atlantic Cities numbers represent only the city proper but, either way, the spread seems massive. Even still, market analysts, such as