But I’d be amiss if I did not suggest that instead you gain knowledge of the aforementioned 3 foundation by studying for a real estate agent/broker license, and then seek employment with REITs, real estate operating companies, real estate managers, or real estate brokers.  

What do you file for this "income overseas," do you file SChedule C self employed on your personal 1040 tax returns ?

According to Statistics Canada, there are 165,900 people employed in Windsor-Essex.

But if employing your family works for you and for them - great, go ahead.

I use the 3x rent for my first barometer, steady employment, good credit, and of course 3 years of rental history.

From what I’ve read in Bloomberg, electing S-Corp taxation for your LLC might reduce your self-employment tax burden when you start paying yourself a salary.

If you have your own business/self-employed you might qualify for a Solo 401(k) or multi-participant 401k whereby you can self-direct into real estate with those funds. 

Registration and Financial Considerations for the Second Company:Is it possible to register the second LLC on the property (as part of the 50%-50% model) if it does not yet have an EIN (Employer Identification Number)?

Quote from @Kevin Akers: Quote from @Brittany Minocchi: Can you qualify full doc (meaning with employment history, income, DTI, tax returns)?

The big pros are the strong job market (lots of major employers), good population growth, and still-reasonable entry prices.