We took the plunge.
I've been a pilot since I was in high-school and I've always said that once I got to old and slow to fly I would buy a sailboat. In 2005 the wife and I did a bareboat charter out of Tortola....we decided we could probably live that lifestyle long term. A couple of years ago the FAA decided they didn't like my EKG so...we're in the process of buying an Omega 36 sloop. The price, finances and insurance have been worked out, just waiting on the survey and sea trial. With the condition of this boat I don't anticipate any major issues.
I've been lurking here for a while but brace yourself for some newbie questions. <G>