I crewed on an H40 ('87 I think) from Cape May, N.J. to Bermuda
. It was a fast capable boat and the passage
was uneventful, but the boat was only a couple of years old at the time.
We also boat-sat an '85 H40 in Grenada
for 2 weeks in 2001 - that boat was the single
biggest thing that convinced us (well, it sure convinced my wife - took about 15 minutes) that we needed a bigger boat than our 34'. If we didn't develop health
issues in 2002, we probably would have bought one. The '80's Hunter
Legend 40s provide an excellent liveaboard
platform for Caribbean
cruising - often better than much newer 40 footers - and they are perfectly suitable for your intended use. All these boats are now 20 years old; and of course, you have to subject them to same scrutiny you would use when considering any boat of that vintage.