No matter how much you plan out your first boat it won't be long before it is the wrong boat . I agree with many of the others. You should get on the wet with something small and cheap. You will learn a million things about boats and boating by meeting other cruisers and seeing what you like and don't like. Even after all that you will still learn alot when you are living on your own boat.
Living on the water is a wonderful adventure. Don't put it off. We both wish we had done it sooner.
After you have your second boat, don't take you wife to boat shows. She will want a different one, and another and another.