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Picture this: the kids are all in college or on their own. You and your spouse have worked like dogs for years and now would like to enjoy life and have fun. Hey, you both still have your health, energy, have held up pretty well and have given 100% to raising your family these past 25 years - now it's YOUR turn!
You have a pretty little house on a lake, fun friends, pleasant neighbors, walking/jogging trails plus various amenities in your community. Your beautiful town has terrific cultural activities, a great variety of restaurants, and the area has plenty of good jobs.
In your opinion and experience - where would this scenario be more likely to occur: Naples, Florida or the Raleigh/Triangle area of North Carolina?
In Florida, any lake in the state can have alligators.
Far away from the coast in NC, you only have poisonous snakes to worry about by the water.
On the other hand I think it'd be sweet to be able to swim anytime of the year in the clear springs with manatees at a perpetual 72 F. Also the lakes ice up quite a bit around the edges during cold snaps in Raleigh. I've seen it.
All of these lifestyle options/amenities are available in both of these communities. With your question "where would this scenario be more likely to occur", I would think it would come down to affordability. With regard to that factor, the Raleigh-Durham-Chapel Hill area has the advantage.
I don't know about NC but I can tell you it cost a bundle to live anywhere near water in FL now. Naples has always been an expensive place to live and if you don't have to worry about moolah there are still the hurricanes. FYI, homeowner's insurance anywhere in FL is ridiculus. A friend who lives on a canal in Clearwater just got her homeowner's insurance bill.. $18K ... a year. There are very few insurance companies writing homeowners in FL so your only choice is state insurance.
I vote NC. Very pretty, moderate weather, nice people and good BBQ. Great antiqueing too. All those small towns have antique stores. Lots of fun and beautiful beaches too.
I've never been to Naples (FLA) but have been to the Triangle. It is a good place to be if you like the South. It has lots of interesting stuff to do, a good museum or three, lots of sunshine, and extremely friendly folk.
My question to myself is "where will I be happiest overall?"
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and have given 100% to raising your family these past 25 years - now it's YOUR turn! 
To me it's the most beautiful place in the world!!!!!!
