I am a licensed captain, and legally (at least from the US) you can't charge someone unless you are licensed.
That being said, why in the world would you pay anything to this captain and then have to work? Don't you see something wrong with this? Take your $2,000 and do a charter in the Caribbean with some friends. The money will be better spent. Then look for a delivery where the most you will have to pay is transportation to and from the boat. Quite honestly, I wouldn't even pay that, but that's because I used to deliver boats for a living. I know what a tough job it can be.