You're best bet is to call a few brokers local to the area and see what they can come up with.It's definitely going to be a surplus or excess carrier that will do it and the premiums will be high. 

@Cole Starin What type of take out financing did you line up to payoff the private money and get into long term perm debt? 

Airbnb gives you the best bet at getting both. 

It's worth investing a few minutes or few hours finding out when so much is on the line. 

You have used home equity lines of credit to purchase investment rentals and want to know the best way to pay down the HELOCs.Between the two properties you bought, after expenses, you have $250 a month positive cashflow to use.What I like to do is pay down some principal every month with my positive cashflow.I use my extra active income from real estate commissions helping other investors to pay down the principal even more which just frees up that credit for me to use again.I know I can refinance the HELOC debt before it changes to principal and interest as it is just interest only payments as yours are.One difference is the cashflow, I have greater positive cashflow and could make the principal and interest payment in the future with the extra cashflow I already enjoy.I always get HELOCs on my income properties as well after purchasing them to pull out as much of my downpayment as possible.

And what is your price point and are you looking for turn-key properties or something along the lines of a "fixer upper"?

Don't be afraid to ask them why they don't want to apply.When I'm having pricing discussions with owners I work with, I always remind them: a month of vacancy costs your bottom line more than a unit filled with a rent reduction.

But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

I haven't seen any statistics to this effect and I don't think any has necessarily been compiled but I bet I wouldn't exaggerate if I state that 95% of the value of real estate in Southern Spain or at least the province of Andalucia is in the Costa del Sol.

Would this be more in line with the "gifting" approach?