You'll first have to narrow down your choices by choosing where in the world to go. There's a lot more than just the Caribbean but it's what's interesting to you. Consider the cultural experiences you could have by going to some of these places. It ranges from cities you've only seen on TV to literally natives in dugout canoes. It's not that difficult to see the latter.
I'd say overall cost (air and boat )and travel time- would be the determining factors rather than quality of the boat and how they dive. Boat cost is actually pretty similar across the world. It flight cost and time to get there that differs. Boat quality, when talking about the major players is probably close to the same minimum level. You can go up from there. Realize that you're talking about going places where people don't do things the same way. Whether it's how they live, the food they eat, or how they act, these things can all be different and not necessarily good or bad.
I think I get a lot more from a LOB experience than just a dive platform. Moving from place to place and seeing new views and diving in amazing locations is just the tip of the iceberg.
I'd suggest considering where you're willing to spend the time and money to fly to and then determine the boats involved. For example, you can go to Fiji but it's 11 hours from LA. And if time and cost aren't an issue, tell me your secret.
And which little boat you dive from in Cocos will be completely inconsequential, because you'll spend most of your time reassembling your wife after that 36 hour trip out to the island!