For Non-Admitted carriers, the important item to then pay attention to is the AM Best rating (or equivalent rating agency).

The amount of equity I call pull is less than the cash I have but not significantly less.When doing this analysis it struck me that it may not be worth using a HELOC for the simple fact that the interest rate is ~9%* while the funds in my high yield account are only yielding ~5%*.

it also means their interest rates change with the Bank of Canada rate. 

You need to be aggressive with your pricing to compete for the few available renters.I recommend dropping our price to $1,750 and offering a month-to-month lease or six-month lease.

If he owes a decent amount on the property, wouldnt the conventional route make him lose whatever interest rate he has?

What is the cap rate?

This would allow you to maximize tax deductions at ordinary tax rates.

Even at a high cap rate you've got several million dollars of market value here, so I'm curious about your base numbers.

That was when the market was stabilized, rates were sub 4.5% and distressed properties actually sold for a significant discount.Today, distressed properties sell for a premium and cash out refi rates are over 8%. 

You can then rent at market rate but have to register it with the town annually and abide by their annual inflation rules.