There seems to be a lot of wannabee cruisers on this and other forums, most of which will never become full-time cruisers. The vast majority of those that I have met over the past decade that are full-time cruisers usually had unique and very marketable skills, or had bankrolled lots of money during their working lives and spending the interest while cruising. Living on Social Security is darned near impossible, but I have come across several elderly couples that live aboard quite comfortably using this as their sole source of income. These individuals are usually tied to a dock, or mooring ball, have great, year round dockage rates and rarely spend time at nite clubs or expensive restaurants.
I know one guy in Boot Key Harbor who is a retired engineer. Shortly after he retired, his company called and asked him to return to work. When he turned them down, they said how about just being a consultant, to which he agreed. He works from his boat using a laptop, fax machine and sat phone. He only works two days a week, and often makes more at consulting than he did when he worked full time, plus he no longer has to commute to Boston.
At one time, I was a full-time, freelance writer, but the print media dried up, fishing in the Mid-Atlantic region went to hell, so I decided to go back to playing music and singing for a living, which was one of the smarter things I've done in my life. It's also a lot more fun than writing and meeting deadlines, and I can usually find work everyplace I've sailed in the US. Unfortunately, the pay scale in the warmer southern climates is lousy, but for the most part, the tips are pretty good, which kinda offsets the lousy pay rate.
So, for all you younger wannabees, now is the time to begin making plans for when you raise the sails and point the bow of the boat south for the winter months. Don't wait till you're too old and infirm to man the helm. My only regret is that I didn't do this 30 years ago.