Were I a potential client, I would not be inclined to charter
a boat that the owner lives aboard. Nor would I be inclined to charter
a boat involved in island hopping. I would be far more inclined to charter a boat working out of a specific port that I wanted to visit. I would not be inclined to contract
with a charter captain
who lacked local knowledge or whose ties to the local community seemed to be transitory.
Whenever I've chartered I've had to make significant deposits well in advance of the charter date. Most of us are not going to be willing to do that for a one-boat operation that doesn't have an established base. My most recent charter required a $1,400 initial deposit that was made nine months in advance in order to secure the dates I wanted. I was happy to do that with the particular company I selected because I felt secure that they would actually be there when I got there.
The business plan reflected in the original post of this thread would not give me the confidence to make such a deposit, which means that his competition would be getting my business rather than him.