Please help me... re: live aboard
We cruised for several years on a simple 30 foot sailboat (4 of us). I remember in Honduras meeting a family of 4 in a 72-foot sailboat that had 2 young people as crew. The man helped with repairs and did a lot of sanding and varnishing. His girlfriend cooked all the meals and provisioned the boat. They both helped care for the kids (8 or 10 years old I think) and helped sail the boat. The dirty work always fell to them ("get that wrench I dropped in the bilge", or "dive down and unwrap that line on the prop"). As I remember they had little experience, but lots of enthusiasm. They were paid a small wage, a few hundred/month for them both, I think and got meals and had separate quarters. They rather enjoyed it, but when I met them, the owner had been in the same anchorage for 3 months and they were tired of the same place. The owner was afraid they would jump ship and leave him without crew (he couldn''t sail the boat without them). There was a little stress.
There are no doubt situations like that available. Being non-sailors won''t help, but you never know. Search the web for people needing crew and you might get lucky. Once you get some experience, you can move up, get licenses, etc, or buy your own small boat and see the world. Lots of people have done it with very little.
As far as travelling to the islands to make a living, it''s not easy unless you have contacts. You won''t legally be able to work and the locals might resent you if you snuck in. Usually when you stop, it''s for a while, so you can get enough $ to stay out for a few months.
I don''t know what bartenders make, but 2 people on a simple boat can live (frugally)on $500/ month in the cheaper places, assuming a paid-for boat with no major repairs needed.
A mentioned before, having a marketable skill, like refrigeration, diesel repair, etc is a way to cruise on a budget. Often the authorities look the other way if your skills are needed or if you advertise quietly.
You probably don''t want to wait to aquire the skills ( I was there too), but you better at least be mechanically inclined if you intend to sail your own boat.
Check into it and if the sea sounds like your thing, move. You need to be around people that do this kind of thing if you want to try it. Iowa ain''t gonna cut it. Try Florida.