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This comment is gonna be an answer to all the comments you've posted, so apologies in advance if its a bit scattershot/accusatory.
I completely respect the desire to raise your kids in Toronto, while maintaining a quality of life approximately equal to your own. However, I'd urge you to reconsider how you view the challenges facing you. I've personally seen the apartment that my grandparents raised their kids in, and they raised 3 children in a small 2 bedroom apartment. Space challenges are almost always actually about the challenge of giving up space, and not about the physical impossibility of fitting in a child.
I'd also like to point out that your career trajectory lines up with your family planning; your (hypothetical) child won't need to have their own room until they're a couple of years old. That matches up with when you expect your salary increases enough to be able to comfortably sustain a 2-bedroom apartment - the best time to have a kid is now, because you'll be able to afford a bedroom for them, when they need it.
These two statements are contradictory with respect to your desire to provide a better life for your children. If Toronto is so much better now than when you were a kid, how could it possibly be a downgrade in quality of life if you raise them up in Toronto now?
As for education, look into IB. Cheaper than Private school, more rigorous than Ontario High Schools.
I agree, Hamilton is underrated, but have you considered the towns in the Greater Toronto Area, such as Burlington, or Oakville? Boring yes, but damn good places to raise a kid.
Thanks for sending me your thoughts!
I have no doubt we could raise a kid here, for a bit. It would be a huge pain, but you are right it's likely the timing would work alright between career progression and the space needs of the family. I mentioned this before, but there is something shitty about having to "downgrade" versus your childhood. Scary thought if there's some job losses and we get stuck here, the den doesn't even have a door.
Honestly, the timing thing you mentioned is a compelling point. I think that's been percolating in my head for a while, and one of the reasons I latched onto this topic. The narrative of "we can't do it yet" is starting to have some cracks in the foundation (is this what brain development feels like?).
This is kind of in the weeds, but the existence of tents in Toronto parks doesn't mean all of Toronto is worse off. The city is bigger and more full of interesting places all over. It just sucks not having a backyard, OR living in a fancier neighborhood. I have never seen tents in Ramsden park (in Forest Hill) for example, but downtown residents don't lean on their city councilors very much (or have the wealth/clout to make their lives suck).
To be honest I find the existence of Burlington and Oakville both mildly offensive to my sense of what makes for a good city (terrible for the environment, unsustainable financially, and deeply opposed to anything changing ever). I don't want my kid to be shackled to me until they're 16, and despite being an avid cyclist in Toronto, I would be very uncomfortable with my kid biking around the streets of Oakville with their friends (not because of crime/stranger danger, because of oblivious drivers and a complete lack of bike infrastructure or respect for cyclists). And they can't walk anywhere because everything is at car distance.
My friends and I were taking the streetcar to and from school in packs at age 11/12, it was great. We could bike (or walk) to each other's houses without riding on or near mega-roads with average speeds north of 60km/h.
Also living in Hamilton means I can at least live and work in downtown Hamilton and have a quick commute. In Oakville or Burlington I'm either taking the GO train into Toronto (awful, especially now that electrification got fucked) or I am driving to some random business park in perpetually worsening YoY traffic (proven to be shitty to your life satisfaction).
This has turned into a shameless downtown elitist rant. Thank you for your perspective. I think you are right, I have not been considering the play you get with timing in the first few year's of your child's life. They don't get born with a need for a full on room to themselves, that takes time.
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