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I think your plan to buy in the cruising ground is a sound one. we've been on the lookout for a few years. sometimes set back by "life". we've just returned from another venture down to sea trial and step on board only to be disappointed....again.
about the boat, your catalina is a good measuring stick to see what works and what doesn't. there are big 34' and small 44'ers. not sure if the book "sensible cruising, the thoreau approach" has been mentioned in this thread. its a great read.
x charter boats are abundant, so are the horror stories of substantial items missed by surveyors, refits gone way over budget, etc. there are good boats available. a passport 40 just sold in the bvi for in the 40k range. (this is the exception rather than rule.)
when evaluating the boat, especially w/gear, look hard at the age of the gear. watermakers can be more expensive to repair than replace.
i dont know if you've set a budget. that dictates the next course of action.
as for your spouse, she will be focused on the safety of the children. its her job.
its a great plan, go get it. we started cruising the bvi with our kids when they were 5 and 8. they're 23 and 26. one ran a 65' catamaran in st thomas and the other just returned from a winter there and is heading back in the fall.
good hunting!
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