What are the most important considerations for a boat buyer?
Flyhop, there are many ways to address your question as ''things to consider'' can range from crew to boat to route issues and back again. Here are a few overarching issues I''d encourage you to tackle...
Families taking time off from work to go cruising can have wonderfully fulfilling experiences (we sure did...), yet they usually need to start from a practical plan that involves an iterative examination of the money needed (for the boat and for the cruising kitty), the time (and timing) which is right for them, and what the Re-entry plan should be. This examination is iterative because each piece ripples its effects into the others, and because each family member''s views need to be folded in, thereby influencing every other member. So...altho'' it''s a more abstract mission than reading a boat book, you might start with some pretty basic steps in this arena. E.g. you might work hard to build a long-term budget that answers the $$ questions (how much to save, how much boat can I buy, how much cushion do I need on re-entry) and let it show you second-order issues (where do we store our ''stuff'' and how much will it cost? do we sell or rent?). You might also treat the family to a big East Coast & Caribbean map from one of the book stores, pin it up on a wall, and start playing ''what if'', something kids can enjoy greatly. What if we visited Jamaica? Is it safe? How do we find out? Which route choices would take us there, and which coast would make the most sense to visit? What do people do there, what''s there to see, and is it expensive or cheap? The Caribbean is a small sea but offers great diversity; it''s far more than just the Bahamas. (BTW Jamaica is a great stop, as are many other island nations).
Re: books, the natural tendency is for us to recommend our favorite ''all about boats'' books and encourage the planning sailor to become a surveyor and savvy buyer as a result. The basic problem with this approach is that authors typically write generically about boat characteristics, systems and design, whereas your needs are quite specific. To complicate things further, your plans can be done by almost any boat (wait until you see some of the boats that got where you are going!), presuming thoughtful preparation and good seamanship. Consequently, the criteria can be fairly broad and forgiving so long as the boat can sail well, is affordable, properly prepared and you have a way to get real-time weather info (hard to come by in the Caribbean if all you have is a VHF), the patience to wait when ''going'' is not comfortable nor easy, and the diligence to watch the weather regularly. So...you might learn a lot about boats by reading ''boat books'' but they may not by themselves be terribly helpful when shopping for your boat.
Here''s a different book suggestion: Buy Bruce VanSant''s _Passages South_, which is about *getting* to the Caribbean from the U.S. east coast (not so much about the places along the way), get each family member to read at least a big chunk of it thoughtfully, and see what it tells you about what you can expect the conditions to be and what you''ll be asking of your boat (and yourselves). Bruce has written, I believe, 8 editions of this book, each one better than the last; it is THE bible and - with reflection - it can tell you a lot about what is important (and not) regarding a boat''s capabilities, key systems, and how to be tactical, careful, and relaxed while having a grand time.
These are only a few ideas; I''m sure there are many more. But here''s a final one: Pick a date. Think in concrete terms, choose an agressive date, and see - for just a while - how it influences the rest of your dreaming and planning. Kids get older and distracted from family events. Parents get older and flabbier and more involved in office politics. Boats get older but never seem to get cheaper, only more expensive. Picking a date can be a valuable catalyst.
Good luck on both the dream and the plan.