If you are nervous about being the delivery captain for the first time, bring along another delivery captain. You will be in charge, but he/she will be there if you get in trouble.
You will not be able to be awake at all times--you will have to have someone else that you can TRUST to be in charge of the
boat when you rest. The required skills for that person are
navigation, watching for traffic, adjusting
sails for conditions, and knowing when to wake you up. I'm not just talking about benign conditions during the day, I'm talking about squalls at 0300. That would be the other delivery captain if you brought one along.
Due to the economics of deliveries, many are done with just two people. If you want to bring another crew along to get experience, you will get more rest. However, you need to spend a good deal of time observing and
training the additional person(s) before you can trust them alone. I've had inexperienced crew who were fast learners, and I've had some who were downright dangerous--I finished those trips pretty tired out.