Relatively small countries, given the right historical breaks, have often ended up punching way out of their weight class. Portugal and Netherlands during the age of exploration are the examples that come most readily to mind. I'm not sure that the size of Haiti is all that probative. Indeed, in Haiti's early history, it controlled the entire island.
As for the techniques of ship construction and sailing, this was the high technology of the day, but it wasn't exactly inaccessible technology. We're not talking designing microchips here.
Here's a sloppy, half baked, seat of the pants timeline for a Super-Haiti.
* Instead of muddling about every which way trying to sort out the situations of whites, maroons and blacks, France, in response to insurrection, reorganizes the place granting universal emancipation, but managing to pacify the planters and and the mulattos.
* Toussaint Louverature does not end up in jail, but accepts the compromise, remaining as effective leader of the place.
* In response to similar pressures from Guadelope and Martinique, France basically installs similar policies and creates the French Caribbean as a series of departments with nominally the same status as French homeland departments. In practical reality, this amounts to a sort of home rule.
* Haiti becomes the fulcrum of French power and operations in the New World, so a portion of the French fleet is stationned there.
* Eventually, the Revolution gets taken over by Napolean, who looks over the place and decides he's got other fish to fry. During the Napoleanic campaigns, Haiti is increasingly left to its own devices, or relied upon to guard other french possessions.
* With the fall of Napoleon, the crushing of the Revolution and restoration of the Monarchy, there's an effort to reinstitute slavery or at least direct control. Doesnt' work.
* Haiti declares independence, France is in no position to enforce, and the British are inclined to support it in order to weaken France in the region. Toussaint takes over. The breakaway also includes the other Caribbean possessions of France, all the way down to French Guiana. It also includes a Haitianized portion of the French navy, giving the Haitians a nucleous of naval power.
* The Latin American revolutions break out. Rioting and insurrection emerges in the Dominican side of Hispanolia. Toussaint moves in and takes over, fairly similar to our timeline. Haiti now controls the resources and population of the whole Island.
* The Haitian takeover of Hispanolia leads to war with Spain, at the worst possible time for Spain - devastated by the Napoleanic wars and beleagured by revolts through the whole of the New World. The Haitian fleet lands first in Puerto Rico, and dislodges the Spanish there. After that, Toussaint begins a Napoleanic campaign for the conquest of Cuba.
* With the expulsion of Spain, Haiti ends up in control of most of the major caribbean islands, except for Jamaica, and sharing the caribbean with only Britain and the Netherlands.
* The next generation sees a period of consolidation and economic rationalisation. The Haitian Empire/Federation adopts creole as its official language, with spanish and french and various hybrid dialects in common use. It remains heavily agricultural, producing rum, sugar, tobacco and coffee for the European and American markets. Nevertheless, there are several attempts to develop a proto-industrial base, particularly in respect of refining agricultural products. But also to build urban infrastructure, particularly fortifications and weapons (memories of wars and revolutions being fresh in everyone's mind). There's a major effort at establishing shipbuilding centres of various sorts, with much emphasis on ships designed for local traffic and communication.
* The Haitians encounter considerable hostility from the United States, which is wrestling with its own slavery issue. On the other hand, relations with the British Empire are quite close - the British tend to see the Haitians as proxy's and catspaws - they've neatly excluded the French and Spanish from the Caribbean, they're a roadblock against the Americans in the region. The downside for the British is that the Haitians are economic rivals producing the same goods and products that the British caribbean colonies do, and giving the local slaves unhappy ideas.
* Relations with the british become increasingly strained and ambiguous over the next few decades. As a result of tensions, the Haitians work to develop their own transatlantic trading fleets and networks.
* The British caribbean possessions become increasingly problematic, there are more and more slave revolts, support for slavery within the British homeland wanes. Britain renounces slavery and emancipates the territories. After this, the British caribbean becomes a net financial drain, unreliable and not terribly useful. The British continue to hold on for strategic purposes. But they take no position and make no objection when the Haitians sweep the Dutch possessions from the Caribbean and South America. The British possessions devolve into informal economic colonies of Haiti and some islands change hands.
* Tensions with the United States remain high and escalate, however. Folowing 1840 and the Mexican American war, arising from economic conflicts, American meddling in British caribbean territories and competition in central america, the Haitian-American war breaks out. American forces land in Cuba, which becomes the principle battlefield. The war also has a naval component, with extensive use of privateers raiding Haitian coastlines and shipping. In return, New Orleans is burned, and the Haitians raid widely along the Gulf of Mexico coasts. The war ends inconcusively, but with the Americans withdrawing from Cuba. This marks the high point of Haitian power. Recriminations after the end of the Haitian-American war contribute to the American civil war.
* The next few decades are ones of stability - there is a 'Homeland' movement to ship freed slaves from America to Haiti, and there is considerable voluntary immigration. Haiti's industrial effort tends to stall out however, with agricultural production and commerce occupying available capital.
* Haitian involvement with central America increases steadily, and the region becomes an informal Haitian colony, although there are competing influences from Mexico and Columbia locally, and from Britain and the United States. In the effort to consolidate control, the Haitians initiate the great Nicaragua Canal Project.
* The canal consumes decades of work and a considerable portion of Haiti's resources. It is completed in 1890, however it never comes close to justifying its immense costs for Haitian society. Haiti is recognized as a world power, expanding its empire displacing Spain in Guam and Hawaii, trade relations with China, and even staking out territories in Africa. Nevertheless, Haiti has long passed its economic peak. In particular, Britain, the United States, Germany and France have left Haiti far behind in terms of industrialization and industrial clout. Haiti's economy is increasingly hidebound and backwards.
* World War 1, when it hits, proves an economic disaster for the Haitians, who find that markets for their agricultural products have collapsed. The Haitians lack the industrial base to be self sustaining. The economic decline continues to worsen through the 1920's, with the Haitian/Nicaraguan canal coming under League of Nations jurisdiction. The depression is painful.
* Oddly, the depression sees the beginnings of reorganization of the Haitian economy, including the imposition of various socialist measures and a concerted effort at Industrial development.
* The Haitians wind up on the right side of WWII, playing a relatively minor role but benefiting economically. The Haitian industrial economy finds ready markets for war production and supply, and expands dramatically. Later after the war, the destruction of German and Japanese industrial bases allow the Haitian manufacturing complexes to continue to thrive.
* Haiti is given considerable credit for the disintegration of the African colonial empires through the 1960's and 1970's, though it is argued that this would have occurred even without their involvement. Haitian diplomacy results in larger consolidated African states, including East Africa, Somali-Ethiopia, West Africa, and Central Africa. In the Caribbean, Jamaica and Guyana opts for independence, but other British possessions end up joining with Haiti, sometimes with a degree of involuntariness. The Haitians acquire their new territories through diplomacy, and manage to avoid Argentina's more aggressive and disastrous approach.
* However, in the later half of the twentieth century, economically, Haiti remains a borderline first world/third world state, heavily dependent upon agriculture, with some relative industrial decline, particularly in comparison to emerging Europe and Asia.
