Cap,

That is really the key, having options and being able to travel between the places you love. That for me would be perfect retirement. I spend time in the woods in Down East Maine, (I call it Negril North) beautiful in the fall but really cold with a ton of snow in winter. May-July bugs / black flies really thick. Having the ability to split the seasons in different locals makes the most sense to me especially if you have people in place to manage your properties when not there. The hills of NC sounds like it is pretty weather optimal (not too hot not too cold). Jamaica, I don't like it I love it, but living there 24/7/365 would probably not work for me.