Most investment properties unfortunately fall under the passive company category in Canada (unless you have five full time employees). 

It’s nice to have one of your employees inside the property 2-3 times a week. 

It's helpful to work with your Property Management Company in order to break down the exact amount of staff needed to service your property through the various stages of a value add strategy, to assign the appropriate estimated hours worked for each of those employees and lastly the estimated dollar per hour wage that each of those employees will receive throughout the hold period.It's so easy to just take an average number for your market, such as $1,200 per door in Market X, but not actually figure out what makes up that $1,200 per door on an ongoing basis as it relates to your specific market and the specific type of project that you will be executing.  

They use their own employees.

That being said you could always look for business in the area that might need STRs for traveling employees or you might just be better off doing a long term rental with any extra space. 

All employees make at least $15/hour over there.

I'm currently considering moving from my position as a contracted employee to a job where I would be a W2 employee.

I personally think a lot of people are not educated on qualified plans; employers just make employees sign up on day 1; crazy. 

As indicated he does not have much time so he has hired an employee (one of his best friends).

Even in a recession the wealthy still have discretionary spending and will continue to use Airbnb's and company's will still send the employees to travel for work so there will be a need there.