Going to reopen this one just to provide some information after going through some of this. The rules are pretty complicated and the only people who really know all the terms and rules thoroughly are the Rent Levelling Board.
Caveating that I’m not an attorney so go seek your own advice but I clarified a few things at a recent rent levelling hearing (which are open to the public and you can find the schedules with a simple Google).
Once you take over a property as an owner occupant, if it is a single family or condo you can live in it for 1 year and that automatically exempts your unit from rent control. You can then rent at market rate but have to register it with the town annually and abide by their annual inflation rules. That then registers the property at a new “base rate” and your future rent increases all be “base rate” + Inflation as guided by the town.
If it’s a multi, you have to live in it 5 years to fully exempt the units. After 2 years you can apply for a “Rent consideration” (I think that’s what they called it) as long as you still live there and that may allow you to increase rents by more than the annual allowance (probably designed for unit that are very low rents). Until then you are supposed to stay at the base rent levels that the units are registered at the time you purchase, and only increase by their guided annual inflation numbers.
Regardless you are supposed to always register your rental unit with the town annually, and be subject to their rent control inflation numbers. STRs are not allowed. Not sure about MTRs.
My general conclusion was that it is tough to do business in the town if your goal is to buy property as pure rentals out the gates and no intention to occupy. If you have offers out on properties, make sure you understand the rent control levels they are under before you buy. The town is encouraging home ownership, so buying a condo/single, living in it for a year plus and then renting out works fine here (what I did), whilst house hacking a multi is more complex.