@Saraya Thornburg there’s always a duplex or triplex opportunity where you can rent out 1-2 units and live in one yourself, not necessarily living roommate style, or maybe a home with a seperate small in law suite or studio that you can rent out to offset costs.

First, it is a lawsuit target. 

@Hoshang Hafizi and @Carson McGeeJust a heads up, there is a rental coalition filing a lawsuit on the 90 day rental minimum portion of Bill 41 that recently passed on O'ahu.  

Your options are lottery, marrying into money, or a multi million dollar lawsuit...

Your other option (just an idea here) is if you purchase another house maybe look for or add an in-law suite to it and they live real close to you, then you rent out the house you currently have also and you solve 2 problems at once, then it allows you to be more flexible with what your parents pay monthly, heck you could even have them pay a/some of the utilities your options at that point are endless, (I do realize some people want their parents/in-laws close but not on the same property was just tossing the idea out there).

If you were forced to sell to cover a lawsuit you’d have about $200k in closing costs and you have $200k in equity.

Some may require legal action, such as a quite title lawsuit, to resolve.

And he has had many people file lawsuits against him for this "training" with many settling out of court. 

Do you have any suggestions/advice on what I should look for in the policy to ensure I'm protected generally protected against a hurricane coming in and blowing the house away, or a guest hurting themselves on the property and filing lawsuits? 

If you fail to follow the rules, you may open your personal assets to a lawsuit.