I would check and see how many 1 bed and 2 bed options there are and what they are priced at because most folks will prefer the full place to themselves so rooming 2 people together could make getting bookings a bit more difficult (not always the case but something to consider)

As long as it meets "minimum" size standards it can look like a broom closet and be considered a bedroom... ridiculous, but it's out there, and in a tight market people will pay for it... 

A majority of people who rent homes here have 100% equity in them so any rent will cash flow. 

Want to repeat what @Mike Terry said for the people in the back. 

If you have the right people in place it can still be done.

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 know people who do this and I do not believe there are issues with it, but speak to an attorney and they should probably notify the company if they are an employee of that company that they are doing this.

I know several people from California who have been purchasing a couple of duplexes in the Midwest each year.

It will be remote, but since you live there now, you probably already have connections who either already know the house or local friends to find you good people to service things as needed.  

Let people live.I answered his question!