Re: Trailer sailer
Wow. What a lot of advise you have gotten since I checked into here last.
I will just say that may family did exactly what you are planning this summer. My wife DOES like boating though so that is a difference. We bought a trailer sailer, 25', and spent nearly our whole summer on it. It cost us 5K in AK where prices are as high as the winter is cold.
Only you can decide what your family is into for fun. If you are an adventurous group then your plans are not really crazy at all. People did it all the time in the 60s and 70s before sailing was displaced by PWCs and powerboats.
Each forum member is going to tell you what they could handle, only you can decide if it is right for your family. The 3 steps above are a great start. My wife a few years ago was a white water guide but was very afraid of the ocean. Now she has kayaked by herself out there, and finished her first 2 sailing classes. You never now what a person will enjoy until they try it.