OP

First decide on whether you are wanting the luxury of a fully crewed charter (Captain and chef), which obviously has a cost that goes along with it. (ie Charter Caribe). And if you are having a chef, you really don't want to eat half meals ashore.

or do you want a captain only (as it does not appear that you have a qualified person in your existing group). Then eating out half the dinners makes more sense. This would be TMM (and others, but the quality of TMM maintenance is impressive as is noted on TTOL frequently).

Then decide which boat(crew) is right for you.

Either way, and you will be in Paradise!