The British managed to take the capital of Cuba because of the incompetent Spanish rulers in the capital. But outside the Capital the Creoles tended to put up more of a resistance. Afterall, it was there home. Spanish rulers lived in Spain. An important one would be the heroe José Antonio Gómez of the town of Guanabacoa. Guanabacoa is located 5 km. SW of the Capital. The British raided the town. José Antonio Gómez after the Capital fell and seeing what happened in his town started a guerilla war on the British. The British had the same problems in the Philippines. Outside Manila there were guerilla groups.
Off topic - The British did better in Trinidad in 1797. The Spanish governor Don José María Chacón seeing that he had few troops and no support from the local population handed the entire island over to the British.
Thinking the same thing would happen in Puerto Rico the British sent a huge invasion force of 68 ships to take over that island in 1797. Veteran troops from the UK. together with some German soldiers of fortune. It is said there were not too many Spanish regulars on that island. But there were plenty of local Natives who many armed just with farming utensils and machetes managed to defeat this huge British force.
Spanish Governor Don Ramón de Castro also would not surrender and knew what he was doing unlike the governors of Trinidad and Cuba om 1763. Spanish King proclaimed something. do not remember, because of the islanders loyalty. They also gave the islanders who wanted, free land.
Interesting. Hadn't heard of the guerilla campaign, I guess there's more resistance than I gave the Cubans credit for.
But if the British are firmly in control of Havana and offer the way for sugar planters to profit (by allowing free trade, which the Spanish never did), how much can the rebels do? The British will make their allies amongst the islanders, so there will be conflict.
Interestingly, even if the Cubans somehow win (I doubt they'd get significant support from the Spaniards, on both a racial basis and wariness of the British), the British companies stationed in the New World would have significant experience fighting against colonial, guerilla, unorthodox fighters... This will certainly change the dynamic of the ARW...