And for an OOS, I always advise to keep things simple at start, don't get greedy, go for quality and consistency, then work on maximizing monetization later. 

Ask yourself: do I really have the knowledge of real estate principles, real estate law and real estate finance; the network of contacts; the experience both in business in general and real estate in particular; the time available; and the analytical ability to compete against FULL TIME EXPERIENCED PROFESSIONALS to be successful in a field where the failure rate is so astronomically high?  

The wrong property management approach will lead to the dreaded three:1) high drama,2) high turnover,3) high property damage.Use Household-led Property Management (HPM) developed and perfected for co-living.5.

Also, there is a need in the marketplace for a co-living PM company that doesn't charge too high of rate. 

However while people in Windsor doesn't have the luxury of high paying jobs that GTA residents have, is it just a temporary fever of buying houses, or there is really something going on in this city ? 

I have an outdoor pool that easily have 1k+ people using it every season and I never had single complaint due to the water quality.

And a high in high season!

Talk to your attorney, and if you dont have one, get one - as @Ken M. said, this is highly specific to the state and the circumstances.

While I do maintain a relatively modest percentage of my assets in money market instruments, corporate debt funds, and high dividend stocks, I remain most comfortable with the investments I specialize in and know best.  

The good news is that it will still serve as a house hack when we move, as there are multiple units on the property.Our concern is that it is in a high fire prone area.