Naples or Fort Myers with a school-age child, what we compared before moving
We came from Mainz two years ago, my husband works for a medical device company on the west coast of Florida, and we have a nine year old. The company gave us a relocation allowance and a list of two cities. We spent three months deciding.
Naples: the school ratings people quote are genuinely high, the streets are clean, the medical infrastructure is excellent. Rent for a three bedroom near the good elementary schools was roughly a third above what we had budgeted, and in season the traffic on the main roads made a fifteen minute drive unpredictable.
Fort Myers: noticeably cheaper for the same square footage, more families with kids our daughter's age, and the drive to his office was shorter. The schools vary a lot street by street, which was the part we as Germans found hardest to accept. At home you go to the school in your district and that is that.
What helped was stopping the comparison of cities and comparing addresses. I spent weeks with https://florida-real.estate/ open, writing down what a house within a fixed radius of each candidate school actually costs, because averages for a whole city tell you nothing when the variance inside the city is bigger.
We chose Fort Myers, north of the river. Our daughter has a friend two doors down and does not remember Mainz much. I still cannot get used to how early the shops close.