My cousin lives in a town near The Villages. She does not have very nice things to say about it. Her biggest complaint is one that my dad experienced in a Chicago suburb that also has a large Del Webb development - The Villages defeat any measures that would assist senior citizens in the community at large because they have those services in their development. For example, there is no paratransit because the residents of The Villages voted it down. Problem is, that means no paratransit for anyone. The other issue with developments like The Villages is the difficulty selling the house, as you are competing with an ever-increasing supply of new housing.
A close friend just moved to a community outside of Clearwater and loves it. She can walk to the beach, stores, restaurants, and the arts center. And no HOAs!