If it's one of the majors like State Farm etc -- I'm thinking they'd offer a rider or endorsement or possibly a different type of policy to cover the property while it's vacant -- are you rehabbing?  

Also factoring in that majority of the tourist come to Oahu not Big Island I think you might have to lower your occupancy rating.  

The majority of contractors probably do residential work straight for the homeowner , ( much better $ ) .

Would it be an issue if I was self-performing a majority of the work myself?

We have a lot going on and this is a major risk and my partner is dead set to do the deal!

I am guessing a lot of owners just collect the rent, defer all the major repairs and expenses, sell and pass them to the next buyers.

Me and my brother purchased a 1941 4-unit in Silver Lake (Los Angeles) back in 2003 for $560K (top of the market at the time, it needed major renovations, and we had to get rid of the existing tenants -- 3% down, 6.5% interest 30 year fixed). 

With all of the major companies based in Washington, it seems to have had a positive impact on the real estate in the area.

In fact, it’s a major factor in your ability to successfully raise money.

Currently we are not interested in selling the home, or making major improvements (yes the 1 bath is not ideal), but instead renting it as-is and see how it goes.