Beartrack,
Have you totally perused the web site for the CDDs? Lots of info on how they operate both now and into the future.
http://www.districtgov.org/ You can also try this link which has information of the difference between the two special CDD's and the residential CDD's. http://thevillagesfl.blogspot.com/
For research maybe you could look into other 55+ communites that have been turned over to the population. Remember, the 110,000 people that will live in TV have a vested interest in keeping up the community since they will need to resell or leave for their heirs to resell.
I think both you and Boomer should rent for a few months to see how you like it and do some digging while you are down here. You don't NEED to buy first if you are worried about buyer's remorse. That's what my wife and i plan on doing.