I agree, but I have tried it. For offshore fishing we run a 28 down east at 18-20 knots to get out 50 miles or so at a reasonable level of comfort. But the goal of that activity is to get to the place we want to put lines in the water as comfortably and fast as possible, because the fun really starts when the lines go in. The goal of a powerboat, for me at least, is to get there.
I've helped deliver some heavy displacement trawlers, and like running in relatively flat seas in the rain and fog while sipping a hot drink with the heat on glancing down at the radar. Some light air days in Maine in the fog/drizzle with rain gear in the cockpit of my little sailboat, I think, gee, a trawler would be nice. But then I remember the sunny day's beating into a 15-20 knot SW in Vineyard Sound, and the desire passes.
But for me, and that's the point here, for me, and not for you, I find trawlers comfortable, but not fun.
Let's also be clear, I'm not a full time live aboard, and never will be. I tried it, I get board. So my priorities are the experience of sailing for a few weeks at a time or even an afternoon. I'd probably think different about these priorities if I was to spend many months or years aboard, or do the passages you do from up here to the Caribbean. But I don't, and don't want to.
We all put our biases based on the way we use our boats into these discussions. I don't think there's a right and wrong way to waste your money on boats, there are just preferences based on how we each use them, and what part of the experience is most important to each of us.
And I also think, for those of us in the northlands, that threads like this give us something to do until the weather gets good