Al, you have the want-to and if you think you have the repertoire, I'd say go for it. I think there is a lot of opportunity out there for someone who is hungry, organized, dedicated, enthusiastic, personable. Especially for you, in Florida.

One of the top priorities, seems to me, is getting your rig down as small, portable and quick to set up as is possible. Plus, learn a lot of popular songs from the 1950s-1970s and even more recent if they were big hits. It never hurts to have a few "old" standards, but to me, focusing on moving the decades forward is apropos if you are going to do senior citizen gigs.
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Bill