Re: Scary night sail
I think that it is wonderful that this all worked out for you and Charlie.
Reading your story, I can see at least 4 points where I would have said "NO!" Maybe it's because I recently got my ticket, but there were many things that were not under your control. As skipper, it is your responsibility to ensure the safety of the crew, and the proper operation of the vessel. If the weather started getting snotty, then this sail could have ended up very differently.
I suggest that you explain to Charlie that you are happy to take him, and friends out on his boat. However, as skipper, you should require that the vessel be properly equipped (adequate dock lines), and that everything work properly. If I were in your position, I would also insist on inviting one crew member with seamanship capabilities with which I was familiar.
Good on ya for being there for your friend... but don't let him take advantage of you.
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USCG Licensed OUPV Captain, ASA 101/103/104/105 Certified Instructor - Also certified in Recreational Marine Electrical Systems