I think generator and A/C is a requirement for a lot of people for the Caribbean - including my family. We're on vacation from the comparably chilly Pacific Northwest and want to be comfortable, or at least able to cool off at our leisure. The genset also provides plenty of electricity for all of our devices and keeps the boat nice and charged up. I do understand that they are expensive and can be a maintenance nightmare though.

Aside from that, one of the first things my wife asks about when chartering is if the heads are electric flushing. She hates pumping the heads and with three kids it is much easier to just push a button. She also likes it when boats have some of the more common small appliances like a blender and regular toaster.

For me I want a boat that has functioning and somewhat current electronics, sails and rigging in good shape, systems that are reasonably easy to operate and make sense and just an overall fun and fast boat (at least relative to other charter boats).

That said, all of the above are nice extras and we would still charter if they weren't available. However, they are things we look for and that will persuade us to charter one boat over another. When it comes down to it we usually just try to find the newest boat we can that ticks the most of those boxes.