I think your background in journalism is coloring your perspective, Flag. Maybe you've had colleagues who either couldn't go to Haiti due to its danger, or you have colleagues who got into the kind of difficult spots you describe once they were there. Journalists are typically dealing in dicier territory than the average traveler.
Of course if Deno just showed up in Port-au-Prince by himself, not speaking kreyole or French, probably everything that you describe would happen to him. I get that you're just trying to keep him safe. But I personally know several dozen people who have gone to Haiti for missionary work, aid work, filmmaking, as part of the Haiti Action Network, and as part of black travel groups over the years (I'm talking 1980s, 90s, 2000s, and now) and none of them have had any of the issues you describe. I, myself, have traveled to other countries just as fraught as Haiti w/out too many issues, definitely no guns in the face.
This is in part b/c these organizations pay off or employ the baddies on the front end to give the travelers a "pass," but the point remains that the risks you describe, while real, can be overcome by proper planning.