Well …

My concern is that a trip to both Cancun and Nassau would raise questions about Cuba. One or the other is common, but who travels to both places in one trip?

The "promoting democratic values to the Cuban people" category means that you travel to Cuba on a structured trip with an international organization that does that type of work. I'm not sure you can claim you're doing that if the question comes up.

You are permitted to go on your own now. You no longer have to go with a group on a people-to-people tour. You are supposed to engage in the types of activities you'd do on a people-to-people tour, though. That means entirely cultural and educational activities. You're not supposed to hang out at the beach, although how would anyone know if you did that? You are required to keep a journal of your activities if you travel this way. In theory, someone from the U.S. government could ask to inspect your journal. I don't know anyone who's been asked, but you are required to keep what you write on hand for five years. I've gone as a journalist and have been upfront about that when I returned to the U.S. No one batted an eye. No one asked to see further evidence of my work.

My gut feeling is that no one will care if you go to Cuba these days. (I can't guarantee anything.) They will care if you're discovered to have omitted something on your customs declaration.