Vinny,
The Villages has a human resources office. There are tons of jobs in the Villages, and it is my understanding that under some circumstances, there is health insurance. My suggestion would be to call the human resources office now and discuss "getting on the job list." Their number is 352-750-5152 there is also a web site at
http://www.careersinthevillages.com/
Hope this is helpful. BTW, I met one of the young women who works in the human resources office and I would have to say that she is one of the most attractive women I have met in a long time. ;D