I have read through the details on this now after commenting on the ACX thread some week back ("private sector Sun Yat Sen"). It looks incredibly appealing, both as a project and on the political level. I'd be happy to help out in some way, though it's not clear in what way I can at this point.
A few questions:
It's my understanding that part of why land reform is so vital is that productivity increases in farmland frees up labour to work higher up the value chain. You mention freeing up liquid capital for previous landowners to invest, and I'm assuming the idea is that this capital helps create those jobs up the value chain. But isn't there a major risk the liquid capital will simply flow out of the island nations into more abstract financial investment abroad? If the landlords are currently sitting at their desk looking at areal footage, I am sure they'll be even happier watching line graphs tracking foreign stocks. I don't know the policy situation in the Lesser Antilles, but I have to imagine they're generally more open economies than mid-century Asia.
Are there any ideas on involving external parties in this? As far as I can see, there are some major international land reform NGOs with interest in the region, and on the study side I can imagine an academic interest in this kind of thing if the land purchases do happen.
It seems to me like a lot of the work here has to be boots-on-ground. You mention local guides and such, but will that be enough? Lots of different languages, cultures and legal statuses among those islands -- are you gonna have to basically start from 0 from nation to nation on the on-location contacts and mapping?
Do you have any recommendations for reading up on land relations in the Lesser Antilles? Most of the stuff I can find right now seems like it'd be more or less dated.