Coverage & Claims
The simple is, yes, you will have to file 2 claims. The damage to your boat would have to be claimed on your boat insurance policy. The liability from the vehicle you were driving is actually what will pay out for the other party's damage, and not the boat insurance liability, since the boat was out of the water at the time of the accident.
The answer will depend on the coverage you currently have on your policy. There are two instances where boat insurance would cover an injury to a passenger caused from falling overboard. If your policy includes medical coverage, your passenger's medical bills should be covered up to the limit on your policy.
While your homeowners policy can extend to boats, it only offers coverage if they are on your property and is normally limited to a dollar amount well below your boat's value. This also doesn't consider the liability that you encounter every time you use your boat.