May 20, 1808 - United States
Secretary of War Henry Dearborn and Secretary of the Navy Robert Smith met - it was quite likely that the United States would be going up against the Franco-Spanish Alliance. This meant figuring out a war strategy, realistically, the United States Navy was unlikely to be able to challenge a Franco-Spanish Battle Line until at least 1810 - furthermore they would likely need more slipways to get building more ships of the line in case something particularly nasty showed up. Right now, they just had USS Patriot and USS Excelsior at their disposal to deal with any ships of the line - and well, the French and Spanish had significantly more ships of the line in service than the United States had building. The only thing that would keep them from completely manhandling the United States Navy was the Royal Navy keeping them bottled up.
However, there was always the chance that could change no matter how remote that the blockade would be broken. This meant that at a minimum, Cuba needed to be taken from the Spanish in order to deprive the Spanish of an easy jumping off point for any counter-invasion. Realistically, if in the future, Spain decides also to take a swing at the United States again, they would need to make Cuba part of the Union to continue depriving the Spanish from such an easy jumping off point to invade the mainland. It was a massive conundrum to be honest, Cuba had a massive population and a significant population of Freedmen. It could throw the politics of the United States into chaos as they would likely be adding a territory with population equal to the state of New York to the Union. But, that was a risk that they would have to take - Smith was actually hopeful that they could make Cuba part of the United States, for then the United States Navy wouldn’t be disbanded again as it would be political suicide to do so.
It was decided that should Congress declare war, Andrew Jackson would lead the invasion of Spanish East Florida while the Navy blockaded Cuba and St. Augustine. Meanwhile, feelers would be sent out to Spanish West Florida to see how they felt about annexation as there was a known quantity of Americans living in the territory. As for Cuba, an army of twenty-five thousand would be raised to invade the island while the US Navy blockaded the major Cuban anchorages: Havana, Santiago, Guantanamo Bay, Nipe Bay, Cienfuegos, Matazanos, and the Bay of Pigs. The Navy would have just enough ships to make it doable.
The biggest problem though would be finding generals capable of leading the invasions as most of the generals who had served in the Revolutionary War were dead - sure many of the officers who had commanded Regiments and Brigades had been recalled as the Army expanded, but this was very much a temporary solution. Yes, West Point had expanded its 1808 class massively, but those new officers wouldn’t hit the Army until 1812 and they needed officers now.