Just to emphasis points that have already been made:-
A 1992 boat is 20 years old. It's going to be coming up for some major maintenance/upgrades/fixing. I seem to recall
the figure of $20k, but a realistic budget
would be 3 or more times that, and the time involved may range from 3 months to 5 years. Even if it comes back with a perfect survey
almost every system may start to fail once full time cruising starts. It's why cruising is sometime described as "fixing boats in exotic locations".
I see that to OP has an older "motor home" so he'll have an idea of whats involved. As a guesstimate his motor
home would have roughly the same interior
space as a 42' sailboat so doubling to the next size up and doubling again 'cause it's a boat and we have maintenance
increasing by a factor of 4.
It's very difficult to get an intuitive grasp of the work involved with keeping a big boat unless you've done it already. Then it's too late!
The other two aspects of the OP's requirement are a heavy displacement
boat with a draft
of less than 6'. The '92 Vauquiez 49 given as an example has a weight of 32,000lb and a draft
of 6', though in real life it could be greater than that. A heavy boat is going to have a deep draft.
Thinking about his requirements the only one that is immutable is that he needs a boat for a family
Thinking about some recommendations if I were in his place I'd look at ex charter
boats in the Caribbean
. It's where he wants to head
, it would save his first voyage from being along what's sometimes called the "thorny path", and the ex charter
boats are much newer and cheaper. I seem to recall
only one instance of an ex charter buyer being less than happy so mostly they don't look too bad. Still need a survey
So my picks are (ex charter):-
38 S2 - not a multi owner myself but for the Caribbean
these look to be almost perfect. A Lagoon
410 would be better for the Pacific, but the 38 should do fine.
2) Beneteau Oceanis
40. There are 2008 boats coming out of charter now and these could just about fit in his budget
and the draft is realistic.
3) Beneteau Oceanis
323. All the good ones are probably gone, but there could be a few left.
4) Beneteau Oceanis 473. To my mind the modern classic cruising yacht. Draft is an issue, but in reality that means a bigger more powerful dinghy
and and oversize anchors with all chain.
For gaining experience I can not imaging anything better than the BVI's/USVI's. He can stay on his boat and take short sails
while sorting out the myriad of problems that even a late model boat in good condition will have.