[smurphny]

One of the most effective ways to lose a friend is to hire him/her to do a job for you. This "free" offer is well intentioned but much more fraught with pitfalls than a friend watering your plants when you're away. If this friend wants to go sailing, leave it at that: you're lending him the boat and he's not doing you any favor, compensated or not. Just make sure your insurance covers lending the boat. Hiring a pro might be a better idea.