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.

But, in these types of transactions clarity is essential in order to structure the deal correctly and to explain to the seller and sub-leasee how the transaction works so lawsuits don't ensue from misunderstand or improperly explained financing. 

Keep in mind the registered agent of an LLC is also the person who receives notice of lawsuits.

Even if a Managing Agent is contracted with the HOA to oversee day to day operations, they typically by law and by their own contracts work "at the direction of the Board", where the ultimate responsibility lies.Your Governing Docs and local laws will determine your options, which are usually Mediation, Arbitration, or Lawsuit.