Not so much for tax reasons, but just for an overall investment/savings with the goal to pay off our main residence as soon as possible.We only have 9 years to pay off the 15 yr mortgage on the condo, which is the rental.

Have any Canadian investors tried to get a US mortgage through using friends in the US? If so, what was the process like and how did you go about it?

A hard money lender has you sign a form that says that the money they are lending on is not a primary home because they can’t lend at hard money rates on a primary residence.

I have found a few multi-family properties I am interested in purchasing, all meeting at least my minimum cash flow numbers and Cash on Cash percentages, however these properties are about 4 hours away from my primary residence.

I have read about surcharging the residents a certain amount (maybe $25-50/month)  Do I just include that in my loan amount or can that just be listed in the lease as a separate expense for the tenants? 

Although you shouldn't need 20-25% down for an owner occupied residence. 

Fast forward my wife and I have new jobs about 45-60 minutes from our current residence.

We require all applicants over he age of 18 that will be living in the residence to have a background check and credit check ran (through Cozy.co) The daughter with special needs is over the age of 18 but morally I do not feel right making her do a background and credit check.

Or is it a complete / private residence for the man and his 17 year old son?

The way I understand the new tax law is that HELOC interest is only deductible when used to build on to, or make repairs to one's primary or secondary residence.