I think it's important to recognize that different boot companies use different lasts and have different design philosophies. They fit different people differently.
Danners might be the best boots in the world, but they dont' fit my feet. It's unfortunate, but it's so. The same might be true for you with Irish Setters (a Red Wing brand BTW, and Red Wing has a solid rep), Brownings, Wolverines, or whatever you can name. Opinions will vary, and some last longer than others, but objectively, they all make perfectly good boots,
especially for a Floridian that won't be wearing them daily for half the year. It's not like you'll wear them out real soon. Irish Setters are great boots -- IF they fit you.
I often go out in my Asolo TPS 535s. Those and the Gore-Tex versions are IMO some of the best boots around -- if they fit YOUR feet.
But they're not insulated. I have 600 gram Thinsulate, Gore-Tex Wolverines that have worked well for me in the cold.
Note that there's a huge difference in what your feet need if you're sitting or standing in cold wind, versus hiking around actively while it happens to be cold outside.
Meindls are good boots, too, of course.
This company in Montana isn't cheap, but they've got what you need:
http://www.kenetrek.com/
I'd go try some on, if I were you. That's step 1.