You ask, I answer: The Caribbean islands are great to port at if coming from or going to somewhere else. For instance, South America circumnavigation or just round the Horn, doing an Amazon trip, doing a partial or complete transit of the Panama Canal.
They are also great for doing a first or second cruise, like the Mexican Riviera can be. But to do either endless times, been there done that, boredom personified otherwise. Especially on a short booze cruise type of experience where the gigantic mega-ships cruise around in circles and visit all ready over crowded ports on occasion. Sorry folks, that isn't the same as ocean cruising or exploration cruising is for me. To each his own.
I also agree with the O.P. that maiden voyages should be avoided, unless you have money and time to spare. After dry dock, I have no problem with those; as far as theme cruises, we have been on only one and again a few times on some with large organized groups which we have had no problem at all with.