Did the boats performance , being different lengths/ performance affect the trip? I would recommend having "sister" boats so likely sail performance similar and one not leaving the other behind.
Also provisioning for both boats needs to take into account where meals will be eaten. 2 separate orders so that you don't have to reshuffle food/drinks along the way (or at least less). Meals onboard can vary with rotation of couples so group has more interaction, or if kids (teenagers) on board, they may be on one boat for dinner with others(adults) on second boat.
Running multiple short dinghy trips is not too much of a factor as everyone not usually ready at same time.... take some and return.
For dinners ashore, splitting up into 2 groups is generally better for your dining than all together, especially for the staff. Anegada (pre-ordering as their general practice) manages larger groups pretty good. Definitely try to plan reservations 2-3 days in advance should help.
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