Another dreamer

Whether it be a charter boat, a rest, a bar, these guys are right as an American if you don't speak super 100% fluent Spanish you are going to lose all your money. It may take a year it may take two but its a loser.
I know lots of guys who shipped down a boat, or a van or this or that. Enjoy the country make your money in the US its far easier. I too dream of starting of a business overseas, but its just a dream, and perhaps "research visits" are a good excuse to get away if you need one.
Look at how many closed down bars and rest. there are down there already .... the rents to a gringo will be high, the locations will be poor. Setting up a business down in C/R you need a wealth of contacts that will be doing favors like fixing the roof, the ref the ice maker, the A/C, the Power. Its not like back home where you call a service guy and they show up at more or less when they promised

Mi favorita Chica just opened a little business it was amazing the way she had basically everyone in town with a trade show up over the course of a week to lend their skill. So one guy taped the wire to the brick, the next guy throws the brick throw the window, ole! you have phone service. I jest a bit, but its not too far from the truth.