As far as I can tell, you're arguing that I should undertake to understand somebody's beliefs about the positioning of all 214,000 miles of coastline in the world before I try to understand their intentions about where they're navigating to.
So, to sum up my response: It doesn't matter. I don't need to know where they think the coastlines are; all I need to know is that they want to go to Jamaica because the weather is nice. And then the information that a hurricane is coming through becomes relevant. If they're going to Jamaica to deliver medical supplies in preparation for that hurricane, that piece of information doesn't add anything.
You seem to be proposing that in an argument about politics, I should engage in a depth-first search. Here's the issue: I can knock down all of their arguments, and change not a thing in their mind. No matter how many "How" arguments are defeated, there are an infinite more laying in wait. To change a mind, you must address the -Why-. You must direct your arguments to their motivations.
You seem to be suggesting I should argue with somebody like this:
"You're going to travel up the sound? You'll hit rocks during low tide, and it looks like that's when you'll be going through. You should go around. And this dock in your itinerary is closed this time of year; you'll need to refuel over here instead. That restaurant right there has terrible food; you should eat here instead..." And so on and so forth, when a good argument might go...
"Oh, you're trying to travel to the peninsula? You'd be better off driving there, the sea route is really inhospitable."
Intentions are destinations. If you don't know what you're talking about, sure, they're worthless - but whether you know what you're talking about or not, it's completely useless to analyze a route if you don't know where that route is intended to lead.
you're arguing that I should undertake to understand somebody's beliefs about the positioning of all 214,000 miles of coastline in the world before I try to understand their intentions about where they're navigating to
I'm not arguing that and I think it's a pretty blatant strawman and that nearly any independent observer of this exchange would agree. This makes me pretty averse to continuing this conversation.
...You seem to be proposing that in an argument about politics, I should engage in a depth-first search. Here's the issue: I can knock down all of
As Multiheaded added, "Personal is Political" stuff like gender relations, etc also may belong here.