Like natural disasters, car accidents, losing jobs, divorces, health issues, lawsuits, injuries, death...

We have a rehab in Orlando and want to make sure that if an injury or other type of claim occurs the GC can't just walk away without being held responsible (using his insurance).

I would especially look for on who knows their stuff when it comes to rental properties and real estate investors.As far as common gaps go when it comes to liability, big one I see is that many landlords do not carry a coverage known as "personal injury" or "personal injury liability".

Liability Insurance – Liability coverage protects the owner and investors in the event an injury occurs at the property.

I suppose you could, but the busy street is supplying all of the customers you could ever want.As for insurance, if you have a standard homeowner's policy on a vacation rental, and a peril occurs - injury, fire, death, car runs through the house, etc., the insurance company is going to deny your claim, as it is a homeowner's policy intended for an owner-occupied home. 

I was unemployed due to a medical injury for a good while, but recently back up and moving the last few months.   

@Raj AhujaI thought about forwarding the bill to the tenant but I didn't want to add insult to injury.

@Eric Alvarez If you’ve obtained any injuries from service, make sure it’s documented in your medical record, and make sure that if you qualify for any disability, you get it, ASAP.

This insures that nobody is going to put a claim in against you for something that is entirely their fault, such as an on-the-job injury or other issue.2. 

I won the suit which was a total shakedown lawsuit but it cost my insurance company a million dollars to defend the lawsuit and we were in jury trial for six weeks.