An extremely detailed scope of work along with an extremely detailed contract, are the keys to a project that is going to finish on schedule and on budget, without surprises. 

The one I'm with has been extremely helpful.

As you might already know, house prices in New York are extremely high, which makes it financially difficult for me to try house hacking here at the moment.

As Jeremy said, it is not just about money- the amount of extreme stress also has to be factored in.

That seems extreme to me, but even if is only 10% of that, that's more than our States entire population, the implications are supermassive. 

I'd done some reading in the past and thought a few of the main Canadian banks had such specialty trust divisions that could help you with plan setup.As for finding investments, networking with other investors, real estate agents, etc. is the way to go.Brian, from what I've heard is that CAN banks  make it extremely difficult to setup. 

Like @Pat Aboukhaled already mentioned, he’s extremely responsive and has excellent market knowledge.

Anything requiring court or judicial decisioning is extremely slow. 

Condo bylaws prevent airbnb usage, so not that.

Tenant screening is a big task and extremely important.