I would guess that the reason you received such a challenging reply from Sailingfool is that you have managed to wrap together a series of choices, each with its own significant risks, into one general question: Should I buy this Seafarer 29 so that my family and I, inexperienced sailors, can go to the Caribbean?
First, let me get to your ultimate goal. Inexperienced tho'' you may be, there''s no reason why you can''t set yourselves the goal of sailing down to the Caribbean in your own small boat. Folks do it all the time, it''s a great adventure if undertaken with the right attitude and skills, and in truth it''s not all that hard provided you take your time, have real-time weather info available to you, and enjoy the anchorages and sights ashore when the weather wants to make it tough.
But...the problem is between where you are NOW and what you want to do THEN, and that''s what Sailingfool is cautioning you about.
The Boat: A Seafarer 29 is not a great choice, with its interior liner, linear galley and dinette (vs. sufficient sea berths), and ''built to a price'' quality. I''m sure it can be done, but this boat is easily improved on.
It''s Age: Moreover, this is a boat that is almost 30 years old. Most of its basic systems (rigging, engine, electronics, sails) may already have been replaced once and could be due for a replacement yet again. This raises two problems: just as you begin your learning curve, lots of repairs can be thrown your way by this used/perhaps tired boat, just when you are much more in need of some fun sailing experiences with your family (for morale purposes and also for learning). AND these mods, repairs and such all cost money, just at a time when you are only learning about the other costs associated with a boat (haulout, berthing fees, perhaps an annual tax or registration fee, new ownership costs for bedding, dishes, foul weather gear, etc.). Again, others have managed to go this route...but it isn''t a great way to begin a fun adventure, with an old boat teaching you hard lessons for a high price.
I disagree with the previous post about ''you first, family second'' insofar as getting out on the water and learning about sailing. If you and your wife (and to the extent it''s possible, your daughter) are committed to this goal as a family, then tackle the learning curve as a family. If one of more of the family find it less and less appealing, better to find out sooner rather than later. Moreover, why hoard all the fun for yourself!? They may enjoy it even more than you do.
The hard truth is that the *idea* of sailing down to the islands may greatly appeal, but the *reality* of what it means, all the good stuff and all the hard stuff, is unknown to you. Many, many people - certainly me, included - have had their dreams fueled by goals they poorly understood...but in the interim, why not set some short term goals that give you a taste of what you think you want to do, at a fraction of the cost of buying a boat, and incrementally work your way towards your ultimate goal. E.g. consider a bare boat charter IN the Caribbean. Or enroll in a sailing school together, mixing it with a vacation week. Or contract for part or all of a week on a privately yacht, in a location you find interesting, where you are promised a mix of instruction and relaxation. Just imagine: if you are paying a boat owner to both teach you sailing and introduce you to boat ownership, but with none of the headaches or costs of owning, navigating or sailing, wouldn''t that be worth a fair penny?
Please let us know what you decide and how it works out for you.