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

Not its saying simple, however its highly possible with the conditions in this market.I can go into detail about the additional million plus people moving to the area, the light rail construction,  and other factors but thats another topic.Same goes with the "trophy numbers".

One,if they have similar properties in the area that may help. the quality of the property is also a factor.

I know there a lot of factors and variables that go in to play but have you seen or have any experience yourselves with making good money in your first year as an agent.

Since I want to buy and hold, rents are an important factor too. 

^^^^^^^^^^^^^^^^^^^^^^FOR STEVEN^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^Everyone;Newbies and seasoned investors and operators, there are four underlying factors of real property.

Then there was the expense of the repairs and a huge depreciation of value (who wants to own in a beautiful area if every other year it needs significant rebuilding?).

Do you have closing costs and holding costs factored?

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

It sounds like it is almost certainly upside down and depending on factors that you don't know about yet, it could be in a position where the bank should be paying you to take it off their plate.