Just as a hypothetical, given our timeline, when would it have been most possible in the 18th or 19th century for Cuba and Puerto Rico to have been acquired/conquered/traded to the United States, and also become states in the Union at any point thereafter?
And a second question, if we say that the US were to include all of Canada from its beginning, could the timeline have sufficiently altered that Spain might be more eager to part with Cuba and Puerto Rico at some point earlier than 1898?
I know Cuba was given the title "La Siempre Fidelísima Isla ", though they did try a rebellion in the 1860s, and later in the 1890s. Perhaps if the US formed closer economic ties to the island in the 18th and 19th centuries, the island may have
Any ideas or possibilities would be appreciated.