Just to be clear: deliveries are not how I make my living (my day jerb is software engineer), but I would sure like to make it my living. It's just a sidegig right now, averaging 2 deliveries per year. I could do more, but there are a lot of boats on which I'd never leave dock for an afternoon picnic, much less going a couple thousand miles in the ocean.

I grew up with and around boats. My family were powerboaters, but I always wanted to sail. So about 16 years ago, I finally bought my first sailboat. And ten years ago, a version of the sailboat after which I lusted since I was a kid came on the market (Formosa 46), in the exact condition I wanted. I crewed on my friends' boats, and as my network grew, people started asking me to sail their boats to a destination. Insurance companies require a licensed captain for deliveries that go into the ocean. So I got my 6-pack + 25 ton captain's license. As time went on, I built up my reputation and sail log. There is no substitute for ticking off miles under the keel. I also did a complete refit, re-rig, and remodel of my own boat, doing all the work myself. That experience goes a long way towards identifying what needs to be done before taking their boat into the ocean and warning the owner (read: reject the job).