I'm licensed here in Nebraska and would be happy to set up a search for you on the MLS with your specific criteria which would send you alerts when new homes are listed or when price drops occur.  

I worked on an events app not too long ago, and it strikes me that scheduling maintenance for a property would be the same as creating, say, a community event at a local church.

In the event of an emergency the tenants need to be able to get out quickly and safely. 

And my lease has language on the frequency and days of the week when showings can occur.

Finally, I would think that people would go to Disney world significantly less when a recession occurs, so also make sure to stress test your business model for this case ...

Don't event have to fly out! 

Hurricanes, earthquakes and floods have recently occurred in places that its never happened to before.  2.

It has occurred to me that the best means for me to get started is a House Hack for my first property to get my REI venture off the ground.

I would invest the upfront effort in self-education (there are a variety of books which will provide you a good primer on real estate in Canada and you have already found one of the more useful sites on the Internet).Once you know which area(s) of real estate investing are of interest to you, look for a local real estate investors association or meeting in Winnipeg and attend an event or two.  

Depending on the nature and degree of the repairs the tenant may have claim to an equitable interest in the property which would make things messy and complicated in the event you need to evict.