I think it really depends on whether you locate to a residential area, or a summer touristy area. The tourist areas, for the most part, will be somewhat barren, and devoid of a community setting that perhaps your kids would like. I'm at opposite ends of the spectrum than you, so I'd replace you in Tampa
Some people are very much at home in the outdoors, and love to ski, whatever. Others are content to hibernate and read, which is fine also. Obviously, if you don't like longer winters, you're barking up the wrong pine tree.
Like everywhere else, you'll find people you don't like, and ones that make you feel at home. I think all states have transplants, some more than others. Check things out in real life, not as a tourist. Come visit the primary towns during the week in the Winni region now, in winter. It's the longest season, so get a feeling for it.