I just posted an article from today's Conway Daily Sun regarding short term rentals and whether they should be regulated in Conway.Check your condo bylaws and be sure you can do short term rentals.

You would have to go to the city, county, state and sometimes even federal regulatory agencies that govern and regulate the particular property you are interested in.

I could generalize but it likely depends on the language of the agreements, regulations, the policies and practices that apply and the parties involved...The authority could likely tell them the policy or what their agreements and terms require in terms of proces in that program if one of two dies.

They are not as regulated as the regular banks are with being stuck in a box.I have had many banks tell me they are getting pounded by regulators with tons of additional compliance controls.

When you arrive at Canada specific question (finance, regulation, taxation), there are active Canadians here on the site who can field them.As for finding a group of investors in the TO area, give a shout to @Gary McGowan who holds monthly REI meetings to see if you might be able to drop in.

The regulations just don't always speak to every situation.

why you wanna be a Super nice landlord...a squeeky fan is not a section 1 requirement to be a feasible living environment but a leaky roof is. 

Things like setbacks, streams, wetlands, and regulations are possible roadblocks that would not apply to an existing house grandfathered in and now affected by things like setback or zoning.

Residential loans are heavily regulated.  

I like to also think in terms of utility costs for the tenants.. so think about areas with long cold winters utls can be very expensive etc.Think about a place like Las Vegas virtually no maintenance in the desert environment.