Does he understand that living on a boat in the Caribbean can be very dangerous with evil people with guns out to kill you and take all you have?
That if he has a weapon on board there are many ports (if not most) where he cannot enter? Or if he does enter, he can have his weapons seized and be jailed by another nation that exerts even more control than ours?
My uncle lived on his sailboat in the Caribbean in the ‘80’s and was well-armed, before both the bad guys increased and the nations outlawed on-board weapons in ports......most of the US is still the safest place on the planet.......
“..living on a boat in the Caribbean can be very dangerous with evil people with guns out to kill you and take all you have?”
Having plied the ocean waves myself, I can attest that the Caribbean is rather ruthless in dealing with lone boaters, and that includes the local constabulary. The coast of Africa can get a little dicey with the piracy going on there particularly on the east coast of Africa, and then there’s Indonesia... The Straits of Malacca & several other places.
In summary, there are real life Pirates that will steal your lunch and pop your bag in a heartbeat. And while in Port in various spots around the globe the thievery will denude your boat of any technology, food, safety gear, Tools, & Fuel while you’re out sauntering about town enjoying the sunset with crappy water in a bottle.