If I am crusing from Bahamas to Azores I would want more then 70 gallons of diesel. Just in case. The 1900 lbs of fuel and water has to be carried down low, but a 37' boat should be able to do it ornot be built. IMO.
The need to fly all possible sail is to me the arguement for a cutter or ketch as the sails are smaller/easier to reef. One awkward fore sail but the others are easier to handle.
Question of Endeavor not really heavy enough, in what respect ? The displacement is heavier then most all the production boats. So where does it need beefing up, if possible ?
Thats why I posted that link, pick it apart please, before I buy one. Looking at cockpits, again, not too hard to pick out the ones built for the close-in cruisers and day sailers. Others otoh, are smaller and have protection.