You definitely don't want to be at The Villages in Florida - too many retired musicians that will play for free, which is pretty much the case with most of the west coast of Florida. Much better along Florida's east coast, the keys, and panhandle where Diki lives.
Of course, you could always set up a weekly gig similar to the one that DNJ has been doing for many, many years. I would do it down here, but that means you would not be able to take an extended vacation, and no matter what, you have to work that night, 52 weeks a year. In the right location, this can be quite profitable, but it does take a lot of legwork in order to get it up and running.
I could easily do this down here, and have been asked by many seniors to do this. It's a matter of finding the right location at a bargain price, then advertising the weekly dance event, doing a lot of promotion in targeted locations, spreading the word. Both DNJ and his wife Nancy keep this weekly event going and work very hard to make it successful. Depending on how you set things up, this can be quite profitable. There are a half-dozen larger halls and catering services that have done this down here, most charging about $8 to $12 per person, including snacks and soft drinks. The cost of the snacks and beverages is minimal at best when purchased at one of the warehouse grocery outlets. If you have 200 people a week, that translates into a hefty profit. Add to that a couple NH/assisted living jobs a week, and the income becomes livable.
Hope this helps,