Great question, all the required deets, very coherent. Kinda’ unusual
You’re going to get a pile of responses.
Because you’re carrying food, you’re pretty well restricted to the Caribbean I think, taking foodstuffs further afield internationally would be more than difficult,
I can think of several very good AI dive resorts in the Caribbean that could cater to almost any dietary need that you specify with advanced notice. you could also likely find any Caribbean liveaboard that with advanced notice could comply with your needs. However, there aren’t that many liveaboards and I don’t see the value in them for the Caribbean.
A liveaboard in the Caribbean seems to be a great waste of money. One should utilize the liveaboard to access Dive sites that are more diverse than simply staying at one resort and going to info their local Dive sites in the Caribbean. This is simply not an issue. There is nothing operating in the Caribbean that gives you better or more access than being at a local dive resort, there have been in the past, but due to the far-flung nature of their stations they’ve gone away. Gone are the days of truly exotic diving via ship in the Caribbean. The better Bahamas liveaboards would be a noticeable exception the ones that get you to the out islands and give you a variety of diving. AquaCat comes to mind.
One thing did make me a little curious & my brow wrinkle ? …and that was your comment about drift diving. This is the similar kind of wording I hear from people who have never skied in deep powder. You might want to try it you might like it …I’m sure you’ll like it if you’re taught correctly. There’s way more to life than skiing on hard pack groomed snow.
Because corals are healthier when they’re in a good stiff current, or changing water, which is presented in currents, you’re gonna see, better looking reefs if you get out there and “go with the flow“
If you could handle some currents …with that budget..,wow - the world is your oyster- but you could start with some more local exotic stuff like Tobago or possibly los Roques.
There are only but two or three natural wrecks in the Caribbean that are existent after being underwater for many years, I understand your lack of desire to do wrecks- but there’s no need to penetrate a wreck to get its advantage - and there’s a lot of wrecks out there that are placed artificial reefs, providing great structure for fish schooling. Same effect as the holy grail status of a seamount, but way easier access.
You’re going to get all sorts of ideas about where to dive and there’s a few things left in the Caribbean that haven’t been totally destroyed, as far as pure accessibility meaning ease of travel, you can’t really beat Roatan or the Bay Islands there is not much current there, but still some of the healthiest reef structures that remain in the Caribbean.