Even though having someone pay your mortgage is great, the short term goal is not just to break even, but to provide highest possible monthly return as well, while those appreciations take place. 

I wish I had been better with money earlier - I had a lot of debt which I refinanced to pay off, otherwise the mortgage would be so low now that it would cash flow easily!

By Nov 2018 .Mortgage was for 64000 current owners 24000.Property would have a value of a minimum of 190 though I know he is a hoarder and the interior will need a lot of work and some work on exterior.

I was told by a mortgage broker that because I own 2 homes CMHC won't insure my mortgage meaning I must put at least 20% down.Any ideas if this is correct or how I can get around this?

Again, you probably want something with a few units at a minimum so that if one goes empty you can still cover the mortgage. 

Or is there a way to assign the property even though theres a mortgage on it?

But this particular house being foreclosed on by the HOA has no mortgage, it was a cash purchase, its vacant and 3 years behind on county taxes. 

I would suggest speaking with a mortgage company, and a local bank to get their advice.

When qualifying for a loan, I’ve heard to go to different mortgage brokers/lenders to compare interest rates.

Is there a mortgage on the property?