Or who you can tolerate and would like to go halves on the vacation Property. 

Take a step, any step, and use the result to identify and take the next step.Step 1: Define your risk tolerance - all relative; high, moderate, or low?

I am also based in vancouver and found the same issue - looked at Squamish, Kelowna, etc. but prices seemed a bit extended for this strategy (for my budget/risk tolerance, anyway) and other interesting towns were farther away and didnt offer the same metrics. 

It really depends on which pockets of town you are looking into - as others have said before on other threads one pocket/neighborhood in San Antonio can vary greatly to another nearby so having boots on the ground sure helps you get a better idea of your tolerance and the surroundings. 

Getting your team set up and being comfortable with it might take multiple trips to the market area, which is an added expense, but if you scale it is a much more tolerable expense.

I also agree with evaluating your risk tolerance and researching regulations (My in-law bought a condo in Green Bay a mile from Packers stadium with AirBnB in mid. 

What is your risk tolerance?

Comes down to risk tolerance and personal preference.

There is risk involved and everyone has different tolerances for risk.

Might depend on your risk tolerance and/or where you want to live.