For most clients choosing a Captain is a once-in-lifetime thing. So many decisions to make. So little experience with which to make them. If you could have the experience of having made the choices, perhaps 100 times, then filtering them down would be a pretty straight forward affair.
 

1. Years of experience
2. Overall variety of experience
3. Weather sense
4. Experience with rough ocean conditions and avoidance of
5. Calm composure in dangerous conditions
6. Methodical about route planning
7. Care in identifying danger ahead of time
8. History of successful deliveries
9. Fine sense of getting a dollar's value from a dollar
10. Aggressive enough to forge ahead
11. Sense to back off rather than hurt the boat
12. Experience with similar route and conditions
13. Dealing with officials
14. Considered reliable by past clients

If you were to ask me for my advice... it's pretty simple. Hire someone you trust, sound them out and check out their references, so that you do trust them. You will NEVER be happy with someone you don't trust and it works both ways. It is not possible to get good results unless there is mutual trust. Distrust is like a corrosive acid. You can't expect your chosen Captain to concentrate 110% on your boat if half his attention is constantly focused on you.
Believe me, it takes 110% concentration to achieve 100% successful delivery trips. The reason so many delivery Captains have such mediocre results, is their lack of attention to the trip itself. A true professional doesn't do the work for the partying that he can get in, but to get the boat delivered, while it's still in one piece!
What we all know, is that it takes only a second's inattention to cause the whole operation to come to grief. To the tune of many thousands of dollars and maybe a life lost.
So... choose wisely!!