It also comes with different level subscriptions that you can continue to up grade as you need more features. 

I have a house, no kids, good income, no debt.

My wife and I own a SFH and a duplex, both house hacks.

Is there one area that is typically viewed as the best option for house hacking? 

Currently I can purchase a 550K home in Toronto with 10% down payment (I am able to save around 30K in a year).2) Should I not buy my first home and continue to live in a rented place and invest that money somewhere else?

Typically you want the debt with the property and putting that debt on your primary is generally a no-no unless its short term.If I were you I'd pull out 70% equity from the rental property, go find another house under market value to fix up and force appreciation. 

From hearing different strategies like BRRR, Fix & Flip, House-Hacking, etc., I've gained most interest in Mid/Long-Term Rentals and BRRR's, and I would most likely want to try to Owner Occupy a House-Hack as my first property. 

So I have an applicant who says she will pay 8 months rent upfront to get the house.

why don't you just house hack the property instead by yourself?

Pregnancy is covered under Fair Housing laws (familial status), so not renting to her (or treating her differently) because of her pregnancy would definitely be prohibited.