I think that you and I are essentially in agreement. Depending on whose published figures you believe, the Moody at roughly 26,400 to 32,000 lbs is roughly 55% to 2/3's of the weight of the Tayana 55. This is an enormous jump in displacement for a small increase in crew. It means that the loads will more than double and the cost of ownership will also more than double. You report that you have much more comfortable passages than smaller boats, but I have to question whether the extra length (from something more moderate at 47 feet to 56 feet) will add to the comfort of the crew when you consider all the factors.
And while you are right that with modern machinery, a small crew can set and fly some very big sails and handle a very big boat, a boat like the Tayana 55 in question was not built with this equipment, but also, this kind of equipment has the habit of failing in the most inopportune times, as in mid-cyclone. Adding to this issue is the remote areas that Johnny is proposing to take this boat.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay