Unfortunately, we've been self-employed in a non-real estate industry for a LONG time now and we couldn't document our income in a way that was sufficient for our lender - so we did a cash deal instead.I thought the equity in that property and in the home we own outright (about $256,000 in total equity) would be enough to reset the conversation for our next deal, but our lender says existing equity will always be overshadowed in our situation by documented income (or lack thereof.)  

She can practice traditional and non-traditional medicine. 

You will qualify immediately after being qualified for a loan to offsetting dept to income ratio.Although, you might find managing a non sophisticated tenant is a huge stress on your main squeeze.

If you have experience with it, would love to hear your thoughts, but that's not my main question.I was looking into an Health Savings Account (HSA) which looks like a great option as well for minimizing medical costs (since most non-premium payments can be deducted via an HSA) but You must have a high deductible health insurance plan to qualify for an HSA. 

Similarly, US lenders are very restrictive even if they are willing to consider lending to Canadians since they  are Non-Resident Foreign Nationals.

What is the minimum downpayment I will need as it will be a non owner occupied loan that I will be trying to find.

The village the house is located in requires an occupancy inspection prior to sale, when the inspector viewed the property, they issued a non-occupancy permit for me to sell the property, but they also want me or the next buyer to pay for 3 permits and fines for work not done without a permit totaling 1k.Several investors talked with the village inspector and they reportedly will work with the next owner to resolve the permit issues without forcing them to tear out the existing work.

Day 5 I told her that we would redraft the contracts but had rethought the situation with the original, non-ESA dog, and that we were asking for $70/month in pet rent.

You could give notice that her rent is going to full market as soon as you take ownership but would prefer having the present owner give her notice to non renew.

Should I agree to pay him a certain sum if i buy a non-listed deal.