It is better to lock interest at historically low rate (4.7%) using government to back the lender than find your "private" bank failed his obligation leaving you with nothing.

I will be retiring from my job soon (gotta love government employment) and will be taking a more active role in my properties than before and want to better organize what I have.  

I keep hearing bits and pieces about a rental strategy that is best called "Renting to the Disabled by the Room for Above Market Rent" that goes something like this: (1) Buy a house with as many legal bedrooms as you can that still has a decent sized common area, (2) rent it out to the relatively high functioning disabled crowd, (3) via some [unnamed] Government program the State pays above market rents for each of the tenets. (4) Send a house keeper 1-2 times per week to ensure the place stays clean and otherwise make sure there are no issues.The up side is: you get above market rent with a much higher than average tenant count.

I provide fully licensed aerial imaging for real estate, infrastructure, government, and marketing purposes via my business Tailwind Productions. 

Kijiji or Realtor for finding deals using a similar method as flippers do (x% ARV)Cornwall is tough because there isn't a lot of inventory and the product that appears affordable is in the east end (usually government assistance).

On just the local level: Job growth and type of jobs, population growth and trends, government planning and development trends, crime, schools, current amount of new building and permits, rent affordability vs home affordability, vacancy rates, taxes.  

Of course not without an equity stake, however there must be some incentive from the government for lenders to provide home loans, correct? 

This is because the federal government is a "sovereign" and they are entitled to something called a "sovereign immunity."

The city will likely be the one to govern short term rental policy. 

No....but most state and local governments charge a transfer tax.