I´m wondering what could happen if the plans of oliver cromwell succed. What if Venables and Penn had been in a better relationship. What if they really succed in the conquer of Sto. Domingo instead of Jamaica. I believe that a conquest, relatively easy, of the island would mean that British troops would be less decimated and much more moral, and may even try the assault on the island of Jamaica and even Cuba. Furthermore, a more developed empire in the Caribbean, would have involved a radical change in the pattern of English colonization, that would lead to a smaller or at least, less important presence in North America, perhaps allowing a better resistance of the French military in the inevitable crash in the area between this two powers.
The sucess of Venables and Penn could might have encouraged more plans of conquest like the one that pretended to take Venezuela, land that only could be supported (by the Spanish) with metropolitan reinforcements because of the winds of the zone, and therefore, could become a consolidated conquest before the Spanish counterattack so more territories in the Caribean, more settlers and less importance of North America.
What do you think?