IMO, it comes down to your own "comfort" level as to whether or not to pay for the "insurance policy" of having a backup generator. What is your goal for the generator? Are you protecting your home (such as in the north where you might want a generator so that you don't lose power/heat and have your water pipes burst)? Since the weather in the Villages does not get that cold for an extended period of time, no worries there. Do you have valuables in your home (paintings for example) that you would be protecting from heat/humidity if you lost your A/C? Are they easily transportable? Or is it that you would not have to worry about having lights, being able to turn your TV on (assuming that your service provider is still operating), throwing out spoiled food from your refrigerator, etc.?
I would submit that you could move to a hotel (yes it might not be in the immediate area), have some nice meals and, yes need to restock the refrigerator-but you could do it multiple times before you would recoup your return on the cost of purchasing and installing the generator. What are the "odds" that a significant power loss will occur that would trigger the need for the generator or to move to other accommodations until power is restored? Anecdotal evidence presented by previous posters indicates that power losses are very uncommon and not long lasting.
I'll defer on discussions of the "big one" scenario as I would presume we might have a lot more to consider than just power. Some people who lived through the tornado that went through our Village couldn't live in their homes due to the damage-if they had a generator, it wasn't doing them any good.
So if you have the money, and would sleep better at night by knowing that you have an "insurance policy" in your back pocket, "git er done". I think that I will use the money for wine, women, and song. Uh, check that, my lovely wife wouldn't like the women part of that........