Oh I'm not negative. I'm all for doing stuff. But Fail to Plan - Plan to fail and all that.
So take the following in the spirit in which it is intended! (Which is jovial with a sprinkling of common sense!)
I have owned and operated a very small conference bike and kayak hire company and had to develop a business plan as part of that. I also had to have insurance and permits for various things. And I know that reality is often totally different from the plan. I had to ignore a load of people telling me I was crazy. But some of the negatives must be taken into account when you plan anything.
I did a little brainstorming and research to contribute. Hope its useful.
A cursory look at
http://www.bahamas.gov.bs puts some of your trading plans in doubt. It seems you need be a resident of the islands in order to be able to run a watersports business. Obviously this is for the benefit of the islanders. There are permits and licences required for trading.
I also don't think being on a trip and running a business at the same time is possible. You might get some beer money but that would be it.
Looks like visas are not required for Americans and Brits.
Is wild camping allowed in bahamas?
Coastguard Regs? America is pretty strict. What are the bahamas like?
Normal Weather conditions in march? Windy enough? prevailing wind?
Have you been following the Danish Family going from Denmark to Turkey? Have a look.
For practicalities - living expenses are pretty cheap when you are camping. You can rent your house while away so mortgages are not an issue. (I do when I go on tour)
What's your sailing background? RYA Tickets? Age? Sex? You have very little Hobie Forum history. These are all valid questions any potential companions need to know. I'm not going sailing with a total newbie and end up holding their hand or end up getting them out of trouble. Or vice versa.
If I were you I would go ahead with a solo practise trip beforehand - record it well, publicise it, even the bad bits and then invite people to join you next time. Get a spot tracker and we can all follow you?
So, Best of luck, I'm sure it will be amazing.
"Better drowned than duffers
If not duffers, won't drown"
Swallows and Amazons
Arthur Ransome