Some will do better but I am skeptical of investment return projections out of line with the rest of the market.My investing approach has always been capital preservation first and aim to hit line drive base hits time after time - over time, you win!

We have come to measure success by the final score, and completely discarding and not enjoying) the success made from the steps along the way.Look at it this way, if (as I believe) you should never be satisfied with where you are, and should always aim to do/be better, and you also believe (which I don't, as I stated above) that success is only measured at the finish line, you will NEVER be successful. 

But I’m ok with fewer properties and decent cash flow when I’m retired in 15 years to supplement my 401k. 

Cozy will not give you the SSN on the report since they use a 3rd party.If possible, try to get their SSN in some part of the application process (Eg: create another supplemental form where the tenant has to enter the SSN).

For myself I aimed for purchasing 3 properties in 2020, I ended up aiming short on closing on 1 and in contract for a second but don't close till the new year.I am super happy with where I am in my real estate journey but going to keep pushing.

There are lots of books that are aimed at the Canadian landscape and all focus on the basics of investing.  

The first situation is what I'm aiming for as house hacking sounds like a great way to get started. 

We're aim to buy in 6-7 months or so. 

You can explain how it can be like supplemental retirement income that he'd get by the month. 

A Bank is effectively the current owner, and even if in your optimistic universe they were to contemplate accepting circa $100k rather than their owed $290k (LOL), such contemplation is likely to take a lot longer than you'd be counting on, meaning that the Contract you would have with the naughty "owner" (whose only aim is to get money out of you), will start burning a hole in your pocket.ie.