Love the title on this thread! It's a great position to be in, eh?
From your recent spending:
- $150- Financial - what does this mean? (bank fees, or savings?)
- $304- Misc/Uncategorized spending - that's high. Is this misc household (ie. decorating, new kitchen things) or misc personal (new clothes, haircuts etc) or something else?
- $250-Shopping - what the heck is this?
I know this is 3 months and comes at a time of upheaval between being away/baby/moving but I'd sink a couple hours into breaking down your whole budget into way more categories. You may decided it's not be worth doing now given the upcoming move, but long-term the budget should probably have a lot more categories (and eventually baby, and potentially rental expenses/income).
I'd suggest: mortgage, food, dining, insurance, gas, parking, transit, each individual bill/utility, various types of misc, various kinds of shopping, health health, personal care 'health', fitness, entertainment, gifts, charity, travel - or whatever combo works for you.
Also, probably obvious, but shop around on car insurance when you move as once out of ON/GTA that should drop significantly.
Out of your giant pile of house cash, I would keep A LOT on hand for now as an emergency fund (given one income, pregnancy, move). Like ~50k in a decent interest earning online bank (I use EQ Bank @ 2.3%). Probably overly conservative, but you can afford it for the next year.
For housing in New City, I vote #2. My understanding is you are familiar with the city, used to live there, and have lots of family support (edited - with your recent post I see this is true). Without any of those, I'd say probably #3, but with those I think #1 and #2 are both doable. But one house with a basement rental seems way more feasible and flexible, and you'd be able to buy in cash if you wanted (contentious point, I know).
I'm a bit biased on that point, since I'm currently a very easy-going basement suite tenant, but I think it's a great situation that can hugely benefit both sides if you find the right fit. For my landlady and us, we keep an eye on each other's places when travelling and such so added bonuses vs. SFH.
Just make sure to read SO MUCH about rental regulations in your new place. And long-term, if you like being a landlord, you can always expand and buy the multi-unit place later. Harder to go back, vs. a basement rental that you could forgo rent from or airbnb or otherwise change up if necessary.
edited: of course, if Mr. HH really wants to go the full time landlord route, buying the multi-unit might make more sense. Added bonus of him having a lot more time/flexibility for the household and baby. I still vote do #2 and consider expanding if it goes well.