That intractable question is not the perennial dinner-party debate about whether Grammar is better than Kings, or Dio tops EGGS. That's utterly irrelevant, either to your child's chances of success in life or to the wellbeing of the nation.
It's about the other end of the school system. There's a mantra everyone knows: education is a ladder to help you climb out of poverty. But it's not true, not in the South, not for the poorest among us. The intractable question is, what are we going to do about that?
By "South", I mean Southside — from Mangere to Manurewa and in all the other parts of South Auckland — but I also mean it metaphorically. The South is where the people who are missing out live, and work, or can't find work. The South exists not only in the south but also in the west, also in parts of the east and the north too.
Nothing will happen in this city unless it happens in the South. We will not become the smart city we need to be until the smartness is available to all.
Auckland has a thousand programmes aimed at making that happen, in the public and private sectors, and there are so many success stories. The Southern Initiative, a council outfit operating out of Manukau, is responsible for some of them. Ateed, the Council's economic development agency, has a specific Southern focus. Many companies are also engaged with the South.
But it's not enough, not nearly enough.
Diseases of poverty have taken stubborn hold. Jobs available to the poor and semi-skilled are so badly paid, many workers have to hold down more than one just to get by.
Domestic violence is a society-wide problem but it's more prevalent among the poor.
Meanwhile, in the well-paid, high-skills sectors of the economy, citizens prosper. And the tax system invites the already prosperous to take up easy tax-free ways to become even more so. The education gap is growing, not shrinking, and who would be surprised?
Salary top-ups and enormously greater resources entice too many good teachers to the so-called elite schools. In the poorest, teachers are dreadfully under-resourced and are blamed for not solving deep and complex social problems.
Making all that worse, they have been undermined by a badly misconceived measuring system. Tellingly, when the Government abolished National Standards late last year there was barely a complaint from anyone. Including the National Party.
Despite the best efforts of many gifted and dedicated teachers and principals, the education system fails too many people. We have to confront this, which means we have to change the way it works.
It comes down to this. What use is a bright shining city, if most of the population are locked out? And who wants to spend their life on either side of a locked gate?
It's not just education. We're really not good, as a city, at talking about this. Again and again, the debate is dominated by the fears of those who have the least to worry about.
It happens in housing, in health, in transport, you name it.
Neglecting the South came to a head at a special meeting of the governing body of Auckland Council last week, called to consider a request for increased funding to build the bases for the America's Cup in 2021.
Most councillors made it clear they welcomed the Cup campaign and they voted for the extra money. But they were also worried.
They wanted to see stronger evidence the event really would provide economic benefits beyond the scope of boat-builders, professional sailors and their mega-wealthy sponsors. They did not believe Emirates Team NZ or the council officials had made the case.
The America's Cup is our moment to discover just how smart Auckland wants to be. We can use it to show off world-leading tech innovations; grow the boat-building industry; provide jobs for thousands; be a tourism magnet; make Auckland "a place where talent wants to live", as Sir Paul Callaghan used to say. And beyond all that, to revel in the fun.
And beyond that again, the Cup is scaffolding to help us with city-building: it's a chance to make Auckland what we want it to be.
So are there plans to transform the city in any particular ways? Curiously, beyond the Cup bases and the Wynyard precinct they're located in, the answer is No. At least, not yet.
A big redesign of Quay Street is already under way, but that was going to happen anyway.
Light rail will not come to Queen Street or be running anywhere else until after the Cup.
The City Rail Link will not be open until after. There's not going to be a big new cultural centre; there's certainly not going to be a new stadium.
With the current state of planning, the America's Cup will showcase a smart city: smart tech, smart sport, smart nightlife. The predictable things.
We could have one new thing, though: a city centre where, if the theory holds, private motor vehicles have been relegated to the margins and city life has been improved for everyone in the process. If the trialling goes well, that will be in place well before the Cup.
Sharpen up: 4 paths to a smarter city
A truly smart city engages all sectors of the economy and society. We need to get a lot sharper at how we do that. Here are four suggestions.
Better business leadership
When we talk about how Auckland might become fit for purpose in the 21st century, why does it so often feel like the big end of town has gone awol? Clinging to old ideas, ducking debates about new ones. Two examples:
● Company car parks. You know about climate change, traffic congestion, public health and making better urban spaces not dominated by cars, right? So why have so few corporates done anything to reduce their employees' reliance on cars and company car parks? Are you waiting for the law to force you to do it?
● The trucking lobby. Transport debates, especially in South Auckland, are dominated by the trucking lobby. Why? The future for diesel-powered freight is clearly limited, as some leading freight firms have been telling us, so when are business leaders as a whole going to step up and lead the call for environmentally and economically sustainable alternatives?
Learn from Lime
E-scooters could turn out to be a genuinely disruptive technology, transforming the way we do short hop journeys. And they're fun.
But their introduction here has been absurd. Although they raise important questions about city-building and how we use our urban space, about safety and about revenue, they've been treated only as a traffic management problem. Officials deep in the bowels of Auckland Transport and the Ministry of Transport have applied the existing regulations mechanically, even to the extent of declaring they cannot be used in cycle lanes.
Worse, although the Lime company is worth billions internationally, they've been allowed to use our public space to enrich themselves while paying almost nothing in fees. How they must be laughing at us.
Could it be more plain that creating a smart city, where disruptive technologies will become more common, is going to require much faster, smarter and more flexible decision-making?
Tax fairness
In a smart city, where a growing proportion of economy activity is created by new-tech industries, an equitable approach to tax is essential.
Look at it this way: every new iteration of the iPhone is a hospital that doesn't get built because nobody collected the tax that should have been due.
Capital gains? Exactly the same thing.
Put ourselves on the map
Every city in the world wants to be a smart city with a low carbon footprint, and many are way further down the track than Auckland. How do we get ahead of the pack? Create something no one else has. Among the possibilities:
● A waterfront stadium sunk into the seabed. The marvel factor: enormous.
● A Museum of the Sea on Wynyard Point, bringing to life, with world-beating technologies, everything from Kupe's astonishing astral navigation to the wizardry of foiling monohulls and beyond. A thrilling celebration of us.
● And that policy to close the streets to cars in order to open them to everyone and everything else. If it's good, really good, that will put us on the map, too.
It's not too late ...
for more ideas, so here's one: why don't we get the kids in?
Require Emirates Team NZ to commit to a whole-of-city engagement with schoolkids. All those kids from the Shore who sail already, and especially all those kids from the South, who don't.
Get them down to Wynyard and introduce them to the wonder of the technologies, the thrills of the sport, the inspiration of the heroic people who do it. Require the challenger teams to take part too, so those kids can also discover the marvels of foreign cultures.
Using the Cup to lift the aspirations of the whole city. Doing it through kids. Doing it for the South, which means doing it for all of Auckland. Somebody should be writing a curriculum for it now.