Thanks for all the replies so far. I appreciate the naysayers, the good
advice from Pelagic and the offer from George DuBose. Please keep the comments coming.
In terms of
insurance, I had a friend of mine use the
boat for a week. My
insurance company only required a letter from me indicating that there were no funds involved (not chartering) and specific permission for him to use the
boat.
By the way, he left it better than he found it, and there were no issues at all. Having said that, I certainly know him personally and trust him.
I still think that within the sailing community there are others who are trustworthy and competent.
Perhaps I'm naive but I think with the proper precautions this might
work.