I have been working with many people who are just trying to get started with real estate investing.

The first thing I want to point out is that it may be wise, in your thinking, to separate the property itself from the STR business that's being run from the property.In the old days (as recent as 10 years ago), people buy a vacation home to enjoy, and they leave it empty when not in use. 

There is so much that goes into buying an STR, especially your first one.

People were falling over crazy to buy anything and driving prices up.

I agree more people need to inquire. 

Down the road as you build equity you can pull it out to buy more real estate. 

How many people are in your “sphere of influence” that will use you to buy or sell without needing to pay for marketing? 

If you are getting buying now in TO & Niagara, you will need to have a large down payment for the units to cashflow. 

A demographic shift with more wealthy people buying there? 

While I could kick myself now, I view it as an invaluable experience because it put me on the receiving end of a close and gave me direct insight into why people sell homes to investors.