Advice will vary considerably. The situation MaryBeth describes seems full of problems. My approach is to take the "step" approach. First, one week out, then three,
then...etc. Much to be learned at each step including living in close quarters. In my humble opinion, one of the biggest factors to get under your belt is learning to change your shoreside(home) routines.
You need to learn to get along without the morning paper and fresh bagels. Those regular Thursday visits from friends or children. Its also amazining how much trip
planning changes once underway. You have to waitout storms, get weather from other sources, and read alot. If you get along on shore, you need to learn if you can get along in close quarters without a lot of personal space.
That aside, the fun part is planning, ships stores, preparing boat, and so on. I too wish I would have done this earlier in life but I didn''t, so now want to go off while in good health and positive mental attitude.