You can get financing for american properties through most of the big 5 banks in Canada. 

But now, you have defeated the reason for doing the  Subject To and have become a lender to someone who probably doesn't qualify for bank financing.

Morgan just launched a new service called "Story" for rent collection, banking, tenant screenings, etc.

Since the banks in Canada do not count your rental income at full value, your GDS/TDS ratios will be out of wack as you get more conventional mortgages and at some point you'll be topped out.

If it's too much you can always move your business to small local banks / credit unions but there is another price to be paid.

Regarding purchasing another house down the road....the "new" bank will want to know what is going on with a mortgage showing up on your credit report. 

Hey Carlo, no question is dumb.I own and self manage one LTR, the mortgage is currently in my name (I'm considering refi into trust) but I currently have all things (banking/finances, lease, etc.) run through a single member LLC. 

But being that they may see the insurance change it might pique their interest in that change … you can always ask them - most banks will gladly advise you of their policies regarding such items 4 plexes are attractive acquisitions… I’m not sure I would bump it to five if it were me.All the best!

She heard what the HML was doing and had a nice HELOC at under 2% sitting there going unused and she decided she'd use the bank's money (the HELOC) to make the float (5% diff plus the 3pts on every deal.

well since banks basically dont do this kind of lending at all for 95% of folks.HML  PML or  money partners is the only way to do it .. short of using your own cash.