“The internet” has lots of information about lots of places, but it certainly seems to be concentrated in a few places. TravelTalkOnline forum is a great place to ask questions at. They don’t have a huge message retention – and maybe that’s best as things change year to year anyhow.
Caribbean Travel Forums is really a collection of links.. it isn’t maintained all that well, so you will find some dead links here and there.
The Sailors Guide to the Windward Islands spiral bound book is a fantastic resource. Be on the lookout for the publication date when buying this book as they publish every few years. They have an updates on their website as well. Very well written books with lots of pictures.
I haven’t found much more good/concentrated information anywhere. There are a few more forums, but are barely used.