@John Friendas - Are you talking about a second mortgage on your owner-occupied property or your existing quadraplex?

As others have pointed out the technology that exists in the space makes communication quite frankly one of the easiest parts of the business at this time and tenants as well as clients have grown accustomed to having quick and efficient communication options at their disposal. 

This option does not exist in the stock market. 

Once you have that foundation, you can start leveraging the equity in your existing properties or look at financing options to expand.

- Does he plan to keep his existing income stream, or would the goal of real estate be to significantly supplement that income? 

It was like that money did not exist.

I have a piece of land behind an existing rental that is almost 1.5 times the size of the standing triplex. 

This amounts to lost opportunity because if you had purchased RE, at the closing it can start producing return. 5) ADUs detract from the existing structure whether this is privacy, a garage, or just yard space. 6) this is related to number 1, but there are many more buyers looking to purchase homes for their family than there are RE investors looking to purchase small unit count properties.

Zach Sikes - Yes, it was subject to assuming the existing financing.

A US/Canada tax treaty might exist that will prevent "double taxation".If you're unable to find someone here or at all let me know I can reach out to a few colleagues that might have a recommendation.