My agent is currently finding best rates with Travelers.   

The higher rates and no point options hopefully are temporary for you until you are able to show a 2 year history of 1099 income, refinance early in 2026 once you have completed your 2025 returns. 

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

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

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.

So, Colorado vacation rentals will be taxed at something between the current residential tax rate of 6.7% and the commercial tax rate of 27.9%.

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. 

Saul, Phoenix and Vegas are popular markets, but I’m not sure they’ll actually cash flow well with today’s prices and interest rates.